Substituted n-(-1,3,4-oxadiazole-2-yl)aryl carboxamides and the use thereof as herbicides

ABSTRACT

Disclosed are N-(1,3,4-oxadiazole-2-yl)aryl carboxamides of formula (I) or the salts (I) thereof as well as the use thereof as herbicides.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is the National Stage entry of International Application No. PCT/EP2018/057268, filed 22 Mar. 2018, which claims priority to European Patent Application No. 17163727.5, filed 30 Mar. 2017.

BACKGROUND Field

The invention relates to the technical field of the herbicides, in particular the field of the heterocyclically substituted arylcarboxamides for the selective control of broad-leaved weeds and weed grasses in crops of useful plants.

Description of Related Art

The herbicidal action of heterocyclically substituted arylcarboxamides is known.

According to the heterocyclic moiety of these compounds, the herbicides of the prior art can be divided into tetrazole- and triazole-substituted arylcarboxamides and oxadiazole-substituted arylcarboxamides.

Document WO 2012/028579 A1 discloses N-(tetrazol-4-yl)benzamides and N-(triazol-3-yl)benzamides which are substituted in the 2-, 3- and 4-position of the phenyl ring and have herbicidal action.

Document WO 2014/184015 A1, too, discloses N-(tetrazol-4-yl)benzamides and N-(triazol-3-yl)benzamides having herbicidal action, and the compounds disclosed in document WO 2014/184015 are substituted at the phenyl ring in position 2, 3, 4 and also in position 5 and 6.

Document WO 2011/035874 A1 discloses oxadiazole-substituted benzamide compounds, namely N-(1,2,5-oxadiazol-3-yl)phenylbenzamides, which are substituted in the 2-, 3- and 4-position of the phenyl ring and have herbicidal action. Further N-(1,2,5-oxadiazol-3-yl)phenylbenzamides are known from EP 0 173 657 A1.

Document WO 2012/126932 A1, too, discloses N-(1,3,4-oxadiazol-2-yl)benzamides, where the benzyl (aryl moiety) is likewise in each case only substituted in position 2, 3 and 4, i.e. the compounds with herbicidal activity known from WO 2012/126932 A1 are not substituted in positions 5 and 6 of the phenyl moiety.

A further document, WO 2017/102275 A1, which, with respect to the present application, is a document according to Art. 54 (3) EPC, discloses further N-(1,3,4-oxadiazol-2-yl)benzamides with the alternative Q⁴=1,3,4-oxadiazol-2-yl. The compounds claimed in WO 2017/102275 A1 are distinguished by a phenyl substituent, referred to as R², which has a diamide structure. The two compounds specified in WO 2017/102275 A1 in a list (Table IV, page 113) were excluded from the scope of the present invention.

Moreover, the starting material used in WO 2017/102275 A1, namely 3-amino-4-bromo-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide, was excluded from the scope of the present invention. This compound, disclosed in connection with Example 3 in WO 2017/102275 A1, has an amino group in the position of the radical Y of the present invention, instead of a radical with diamide structure.

In addition to the three compounds mentioned above, the scope of the present invention excludes six further commercially available compounds. For these six compounds, no use of the compounds as herbicide was found in the prior art.

However, the known N-(1,3,4-oxadiazol-2-yl)benzamides frequently have insufficient herbicidal activity.

SUMMARY

Accordingly, it is an object of the present invention to provide further N-(1,3,4-oxadiazol-2-yl)benzamides having improved herbicidal activity.

The object is achieved by N-(1,3,4-oxadiazol-2-yl)arylcarboxamides according to claim 1, i.e. by N-(1,3,4-oxadiazol-2-yl)arylcarboxamides of the formula (I) or salts thereof

where the substituents have the following meanings: A represents N or C—Y, R represents hydrogen, halogen, (C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, CH₂R⁶, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, OR¹, NHR¹, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methylcarbonyl, trifluoromethylcarbonyl, dimethylamino, acetylamino, methylsulfenyl, methylsulfinyl, methylsulfonyl or represents heteroaryl, heterocyclyl, benzyl or phenyl, in each case substituted by s radicals selected from the group consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, X represents nitro, halogen, cyano, formyl, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, C(O)NR¹OR¹, OR¹, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)- alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², NR₁R₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂, (C₁-C₆)-alkyl-heteroaryl, (C₁-C₆)-alkyl-heterocyclyl,

-   -   where the two last-mentioned radicals are each independently of         one another substituted by s radicals selected from the group         consisting of halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,         S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, and         where heterocyclyl carries n oxo groups,         Y represents hydrogen, nitro, halogen, cyano, thiocyanato,         (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,         halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,         (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,         halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,         halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, COOR¹, OCOOR¹,         NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, O(CH₂)₂—NH(CO)NMe₂,         O(CH₂)₂—NH(CO)NHCO₂Et, OC(O)N(R¹)₂, CO(NOR¹)R¹, NR¹SO₂R²,         NR¹COR¹, OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂,         N═S(O)_(n)R⁷R⁸, S(R⁹)═NR¹⁰, S(O)(R⁹)═NR¹⁰,         (C₁-C₆)-alkyl-S(O)_(n)R², C(R¹¹)═NOR², (C₁-C₆)-alkyl-OR¹,         (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,         (C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,         (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,         (C₁-C₆)-alkyl-NR¹SO₂R², N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂,         (C₁-C₆)-alkyl-phenyl, (C₁-C₆)-alkyl-heteroaryl,         (C₁-C₆)-alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl,     -   where the last 6 radicals are each independently of one another         substituted by s radicals selected from the group consisting of         halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,         (C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,         halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and         cyanomethyl, and where heterocyclyl carries n oxo groups,         Z represents hydrogen, nitro, halogen, cyano, thiocyanato,         (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkyl,         (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,         halo-(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,         halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,         halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹(O)C, R¹(R¹ON═)C,         R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N,         R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R²(O)_(n)S, R¹O(O)₂S,         (R¹)₂N(O)₂S, (R⁵O)₂(O)P, R¹(O)C—(C₁-C₆)-alkyl,         R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl,         NC—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl,         R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl,         R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl,         R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl,         (R¹)₂N(O)₂S—(C₁-C₆)-alkyl, (R⁵O)₂(O)P—(C₁-C₆)-alkyl, phenyl,         heteroaryl, heterocyclyl, phenyl-(C₁-C₆)-alkyl,         heteroaryl-(C₁-C₆)-alkyl, heterocyclyl-(C₁-C₆)-alkyl,     -   where the six last-mentioned radicals are each independently of         one another substituted by s radicals selected from the group         consisting of halogen, nitro, cyano, thiocyanato, (C₁-C₆)-alkyl,         halo-(C₁-C₆)-alkyl, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S,         (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, and     -   where heterocyclyl carries n oxo groups,         with the proviso that at least one of the radicals Y and Z does         not represent hydrogen, i.e. that in the positions of the         radicals Y and Z of the compound (1) either only Y or only Z may         represent hydrogen,         V and W independently of one another are selected from the group         consisting of hydrogen, cyano-S¹, halogen, nitro, (C₁-C₈)-alkyl,         (C₃-C₇)-cycloalkyl, (C₃-C₇)-cycloalkyl-(C₁-C₄)-alkyl,     -   where the (C₃-C₇)-cycloalkyl groups in the two abovementioned         radicals are unsubstituted or partially or fully halogenated by         a halogen selected from the group consisting of fluorine,         chlorine, bromine and iodine,         (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, (C₁-C₈)-haloalkyl,         (C₁-C₃)-alkylamino, (C₁-C₃)-dialkylamino,         (C₁-C₃)-alkylamino-S(O)_(n)(C₁-C₃)-alkylcarbonyl,         (C₁-C₈)-alkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,         (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy-S¹,         (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,         (C₁-C₄)-alkylthio-(C₁-C₄)-alkylthio-S¹, (C₂-C₆)-alkenyloxy,         (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkoxy,         (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl,         (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkoxy-S¹, S²—S(O)_(n)—S₁, phenoxy-S¹         and heterocyclyloxy-S¹,     -   where heterocyclyloxy represents a 5- or 6-membered monocyclic         ring or an 8-, 9- or 10-membered bicyclic saturated or partially         unsaturated or aromatic heterocycle attached via oxygen which         has 1, 2, 3 or 4 heteroatoms as ring atoms selected from the         group consisting of O, N and S, and     -   where the cyclic groups in the case of phenoxy and         heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4         identical or different radicals selected from the group S³,         with the proviso that in each case at least one of the radicals         V and W does not represent hydrogen, i.e. that in the positions         of the radicals V and W of the compound (1) either only V or         only W may represent hydrogen,         S¹ represents a covalent bond or (C₁-C₄)-alkanediyl,         S² represents (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl,         (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,         (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, phenyl or heterocyclyl,         where heterocyclyl represents a 5- or 6-membered monocyclic         saturated or partially unsaturated or aromatic heterocycle which         1, 2, 3 or 4 heteroatoms as ring atoms selected from the group         consisting of O, N and S, where phenyl and heterocyclyl are         unsubstituted or substituted by 1, 2, 3 or 4 identical or         different radicals selected from the group consisting of         halogen, (C₁-C₆)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and         (C₁-C₄)-haloalkoxy,         S³ represents halogen, nitro, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl,         (C₃-C₇)-halocycloalkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,         (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,         (C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,         (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,         (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,         (C₃-C₇)-cycloalkoxy or (C₁-C₆)-haloalkyloxy,         R¹ represents hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,         (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,         (C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,         (C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,         (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,         heteroaryl, (C₁-C₆)-alkyl-heteroaryl, heterocyclyl,         (C₁-C₆)-alkyl-heterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,         (C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,         (C₁-C₆)-alkyl-NR³-heterocyclyl,     -   where the abovementioned radicals R¹, except for hydrogen, are         substituted by s radicals from the group consisting of cyano,         halogen, nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³,         COR³, OCOR³, SCOR⁴, NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂         and (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and     -   where heterocyclyl carries n oxo groups,         R² represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,         (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,         (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,         (C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,         (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,         heteroaryl, (C₁-C₆)-alkyl-heteroaryl, heterocyclyl,         (C₁-C₆)-alkyl-heterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,         (C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,         (C₁-C₆)-alkyl-NR³-heterocyclyl,     -   where the abovementioned radicals R² are substituted by s         radicals from the group consisting of cyano, halogen, nitro,         thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³,         SCOR⁴, NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and         (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and     -   where heterocyclyl carries n oxo groups,         R³ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,         (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl or         (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,         R⁴ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,         R⁵ represents methyl or ethyl,         R⁶ represents acetoxy, acetamido, N-methylacetamido, benzoyloxy,         benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl,         benzoyl, methylcarbonyl, piperidinylcarbonyl,         morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl,         methylaminocarbonyl, dimethylaminocarbonyl, (C₁-C₆)-alkoxy,         (C₃-C₆)-cycloalkyl, or represents heteroaryl, heterocyclyl or         phenyl, in each case substituted by s radicals from the group         consisting of methyl, ethyl, methoxy, trifluoromethyl and         halogen,         R⁷ and R⁸ each independently of one another represent         (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,         (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,         phenyl, heteroaryl or heterocyclyl,     -   where the three last-mentioned radicals are each substituted by         s radicals from the group consisting of nitro, halogen, cyano,         thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,         (C₃-C₆)-cycloalkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N,         R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, and     -   where heterocyclyl carries n oxo groups,         or         R⁷ and R⁸ together with the sulfur atom to which they are         attached form a 3- or 8-membered unsaturated, partially         saturated or saturated ring which, in addition to the carbon         atoms and in addition to the sulfur atom of the sulfoximino         group, in each case contains m ring members from the group         consisting of N(R¹), O and S(O),     -   where this ring is in each case substituted by s radicals from         the group consisting of nitro, halogen, cyano, thiocyanato,         (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O(O)C,         (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and         R¹O—(C₁-C₆)-alkyl, and     -   where this ring carries n oxo groups,         R⁹ represents (C₁-C₆)-alkyl substituted by s radicals from the         group consisting of halogen, (C₃-C₆)-cycloalkyl and R¹¹O,         R¹⁰ represents hydrogen, cyano, R¹¹(O)C or (R¹¹)₂N(O)C,         R¹¹ represents hydrogen, (C₁-C₆)-alkyl or halo-(C₁-C₆)-alkyl,         R¹² represents hydrogen, cyano, (C₁-C₆)-alkyl,         (C₃-C₆)-cycloalkyl, halo-(C₁-C₆)-alkyl, OR⁸, SR⁸ or NR⁸R⁹,         m represents 0, 1 or 2,         n represents 0, 1 or 2, and         s represents 0, 1, 2 or 3,         with the proviso that the compounds

-   4-bromo-3[[(diethylamino)carbonyl]amino]-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,

-   4-bromo-3[[(ethylmethylamino)carbonyl]amino]-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,     and

-   3-amino-4-bromo-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,     and also

-   4-bromo-2,6-difluoro-2-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,

-   4-bromo-2,6-difluoro-2-N-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)benzamide,

-   3-amino-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,

-   2-amino-6-fluoro-2-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3     nitrobenzamide,

-   2,6-difluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3 nitrobenzamide, and

-   3-amino-2,6-difluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide     are excluded.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

The N-(1,3,4-oxadiazol-2-yl)arylcarboxamides of the invention differ from the known N-(1,3,4-oxadiazol-2-yl)arylcarboxamides in particular by the additional substituents in positions 5 and 6 of the phenyl moiety.

The core of the invention relates to the surprising discovery that, in the case of the N-(1,3,4-oxadiazol-2-yl)arylcarboxamides, the phenyl substituents in positions 5 and 6 of the phenyl are, in combination with the other substituents, of unexpectedly high relevance for the herbicidal activity.

In the formula (I) and all the formulae which follow, alkyl radicals having more than two carbon atoms may be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n-propyl or isopropyl, n-, iso-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Halogen is fluorine, chlorine, bromine or iodine.

Heterocyclyl is a saturated, partly saturated or fully unsaturated cyclic radical which contains 3 to 6 ring atoms, of which 1 to 4 are from the group of oxygen, nitrogen and sulfur, and which may additionally be fused by a benzo ring. For example, heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl.

Heteroaryl is an aromatic cyclic radical which contains 3 to 6 ring atoms, of which 1 to 4 are from the group of oxygen, nitrogen and sulfur, and which may additionally be fused by a benzo ring. For example, heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl, 2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4-tetrazolyl, 1,2,3,4-oxatriazolyl, 1,2,3,5-oxatriazolyl, 1,2,3,4-thiatriazolyl and 1,2,3,5-thiatriazolyl.

If a group is polysubstituted by radicals, this should be understood to mean that this group is substituted by one or more identical or different radicals selected from the radicals mentioned.

Depending on the nature of the substituents and the manner in which they are attached, the compounds of the general formula (I) may be present as stereoisomers. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Stereoisomers likewise occur when n is 1 (sulfoxides). Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation processes. It is likewise possible to selectively prepare stereoisomers by using stereoselective reactions with use of optically active starting materials and/or auxiliaries. The invention also relates to all the stereoisomers and mixtures thereof that are encompassed by the general formula (I) but are not defined specifically.

Preference is given to compounds of the general formula (in which A represents N or C—Y, where

R represents hydrogen, halogen, (C₁-C₄)-alkyl, halo-(C₁-C₄)-alkyl or (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,

X represents nitro, halogen, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, OR¹, S(O)_(n)R², (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkyl-heteroaryl, (C₁-C₆)-alkyl-heterocyclyl,

-   -   where the two last-mentioned radicals are each substituted by s         radicals selected from the group consisting of halogen,         (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl,         (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, and where heterocyclyl         carries n oxo groups,         Y represents hydrogen, nitro, halogen, cyano, thiocyanato,         (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,         halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,         (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,         halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,         halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, COOR¹, OCOOR¹,         NR¹COOR¹, C(O)N(R¹)₂, OC(O)N(R¹)₂, CO(NOR¹)R¹, NR¹SO₂R²,         NR¹COR¹, OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂,         N═S(O)_(n)R⁷R⁸, S(R⁹)═NR¹⁰, S(O)(R⁹)═NR¹⁰,         (C₁-C₆)-alkyl-S(O)_(n)R₂, C(R¹¹)═NOR¹², (C₁-C₆)-alkyl-OR¹,         (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO2R², (C₁-C₆)-alkyl-CO₂R¹,         (C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,         (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,         (C₁-C₆)-alkyl-NR¹SO₂R², N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂,         (C₁-C₆)-alkyl-phenyl, (C₁-C₆)-alkyl-heteroaryl,         (C₁-C₆)-alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl,     -   where the six last-mentioned radicals are each substituted by s         radicals from the group consisting of halogen, nitro, cyano,         (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,         S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,         (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and where         heterocyclyl carries n oxo groups,         Z represents hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl,         (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,         halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,         (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,         (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,         halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹(O)C, R¹(R¹ON═)C,         R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N,         R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R²(O)_(n)S, R¹O(O)₂S,         (R¹)₂N(O)₂S, (R⁵O)₂(O)P, R¹(O)C—(C₁-C₆)-alkyl,         R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl,         NC—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl,         R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl,         R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl,         R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl,         (R¹)₂N(O)₂S—(C₁-C₆)-alkyl, (R⁵O)₂(O)P—(C₁-C₆)-alkyl, phenyl,         heteroaryl, heterocyclyl, phenyl-(C₁-C₆)-alkyl,         heteroaryl-(C₁-C₆)-alkyl, heterocyclyl-(C₁-C₆)-alkyl,     -   where the six last-mentioned radicals are each substituted by s         radicals selected from the group consisting of halogen, nitro,         cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R¹O,         (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl,         and where heterocyclyl carries n oxo groups,         with the proviso that at least one of the radicals Y and Z does         not represent hydrogen,         V represents hydrogen, halogen, cyano, nitro, (C₁-C₄)-alkyl or         (C₁-C₄)-haloalkyl,         W represents halogen, cyano, nitro, (C₁-C₄)-alkyl or         (C₁-C₄)-haloalkyl,         where R¹ to R¹² and m, n and s are each independently of one         another as defined in claim 1, with the proviso that the         compounds

-   3-amino-4-bromo-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,

-   4-bromo-2,6-difluoro-2-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,

-   4-bromo-2,6-difluoro-2-N-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)benzamide,

-   3-amino-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,

-   2-amino-6-fluoro-2-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3     nitrobenzamide,

-   2,6-difluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3 nitrobenzamide, and

-   3-amino-2,6-difluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide     are excluded,     where R¹ to R¹² and m, n and s are each independently of one another     as defined above.

Particular preference is given to compounds of the general formula (I) in which A represents N or C—Y, where

R represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl or halogen,

X represents nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, ethylsulfanyl, ethylsulfinyl, ethylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxyethoxymethyl, cyclopropylmethoxy, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl, Y represents hydrogen, nitro, fluorine, chlorine, bromine, iodine, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, OR¹, S(O)_(n)R², SO₂N(R¹)₂, N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)- alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkyl-phenyl, (C₁-C₆)-alkyl-heteroaryl, (C₁-C₆)-alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl,

-   -   where the six last-mentioned radicals are each substituted by s         radicals from the group consisting of halogen, nitro, cyano,         (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,         S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,         (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and     -   where heterocyclyl carries n oxo groups,         Z represents hydrogen, nitro, cyano, fluorine, chlorine, bromine         or iodine,         methyl, ethyl, n-propyl, isopropyl, cyclopropyl,         trifluoromethyl, difluoromethyl, chlorodifluoromethyl,         dichlorofluoromethyl, trichloromethyl, pentafluoroethyl,         heptafluoroisopropyl, methoxy, ethoxy, methylsulfanyl,         methylsulfinyl, methylsulfonyl, ethylsulfanyl, ethylsulfinyl,         ethylsulfonyl or 1H-1,2,4-triazol-1-yl,         with the proviso that at least one of the radicals Y and Z does         not represent hydrogen,         V represents hydrogen, fluorine, methyl or trifluoromethyl         (CF₃),         W represents fluorine,         where R¹ to R¹² and m, n and s are each independently of one         another as defined above.

Very particular preference is given to N-(1,3,4-oxadiazol-2-yl)arylcarboxamides of the formula (I) in which A represents C—Y, where

V represents hydrogen,

W represents fluorine

and the radicals

R, X, Y and Z as well as the radicals R¹ to R¹² and also m, n and s are each independently of one another as defined above.

Even more preference is given to N-(1,3,4-oxadiazol-2-yl)arylcarboxamides of the formula (I) in which A represents C—Y, where

R represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl or chlorine,

X represents nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, ethylsulfanyl, ethylsulfinyl, ethylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxyethoxymethyl, cyclopropylmethoxy, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl, Y represents hydrogen, nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, OC(O)N(R¹)₂, CO(NOR¹)R¹, NR¹SO₂R², NR¹COR¹, OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, N═S(O)_(n)R⁷R⁸, S(R⁹)═NR¹⁰, S(O)(R⁹)═NR¹⁰, (C₁-C₆)-alkyl-S(O)_(n)R₂, C(R¹¹)═NOR¹², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO2R², (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂, (C₁-C₆)-alkyl-phenyl, (C₁-C₆)-alkyl-heteroaryl, (C₁-C₆)-alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl,

-   -   where the last 6 radicals are each substituted by s radicals         from the group consisting of halogen, nitro, cyano,         (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,         S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,         (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and where         heterocyclyl carries n oxo groups,         Z represents hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl,         (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,         halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,         (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,         (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,         halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹(O)C, R¹(R¹ON═)C,         R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N,         R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R²(O)_(n)S, R¹O(O)₂S,         (R¹)₂N(O)₂S, (R⁵O)₂(O)P, R¹(O)C—(C₁-C₆)-alkyl,         R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl,         NC—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl,         R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl,         R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl,         R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl,         (R¹)₂N(O)₂S—(C₁-C₆)-alkyl, (R⁵O)₂(O)P—(C₁-C₆)-alkyl, phenyl,         heteroaryl, heterocyclyl, phenyl-(C₁-C₆)-alkyl,         heteroaryl-(C₁-C₆)-alkyl, heterocyclyl-(C₁-C₆)-alkyl,     -   where the six last-mentioned radicals are each substituted by s         radicals from the group consisting of halogen, nitro, cyano,         thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R¹O, (R¹)₂N,         R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, and         where heterocyclyl carries n oxo groups,         with the proviso that at least one of the radicals Y and Z does         not represent hydrogen,         V represents hydrogen,         W represents fluorine and         R¹ to R¹² and m, n and s are each independently of one another         as defined in claim 1,         with the proviso that the compounds

-   3-amino-4-bromo-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,

-   4-bromo-2,6-difluoro-2-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,

-   4-bromo-2,6-difluoro-2-N-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)benzamide,

-   3-amino-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,

-   2-amino-6-fluoro-2-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3     nitrobenzamide,

-   2,6-difluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3 nitrobenzamide, and

-   3-amino-2,6-difluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide     are excluded.

Even more particular preference is given to N-(1,3,4-oxadiazol-2-yl)arylcarboxamides of the formula (I) in which A represents C—Y, where

R represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl or chlorine,

X represents nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, ethylsulfanyl, ethylsulfinyl, ethylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxyethoxymethyl, cyclopropylmethoxy, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl, Y represents hydrogen, nitro, fluorine, chlorine, bromine, iodine, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, OR¹, S(O)_(n)R², SO₂N(R¹)₂, N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)- alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkyl-phenyl, (C₁-C₆)-alkyl-heteroaryl, (C₁-C₆)-alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl,

-   -   where the six last-mentioned radicals are each substituted by s         radicals from the group consisting of halogen, nitro, cyano,         (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,         S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,         (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and     -   where heterocyclyl carries n oxo groups,         Z represents hydrogen, nitro, cyano, fluorine, chlorine, bromine         or iodine, methyl, ethyl, n-propyl, isopropyl, cyclopropyl,         trifluoromethyl, difluoromethyl, chlorodifluoromethyl,         dichlorofluoromethyl, trichloromethyl, pentafluoroethyl,         heptafluoroisopropyl, methoxy, ethoxy, methylsulfanyl,         methylsulfinyl or methylsulfonyl, ethylsulfanyl, ethylsulfinyl,         ethylsulfonyl or 1H-1,2,4-triazol-1-yl,         with the proviso that at least one of the radicals Y and Z does         not represent hydrogen,         V represents hydrogen,         W represents fluorine and         R¹ to R¹² and m, n and s are each independently of one another         as defined above, where in particular for the radicals R¹ and         R²:         R¹ represents hydrogen, (C₁-C₆)-alkyl or (C₁-C₆)-haloalkyl,     -   where the above-mentioned radicals R¹, except for hydrogen, are         substituted by s radicals from the group consisting of cyano,         halogen and nitro,         R² represents (C₁-C₆)-alkyl or (C₁-C₆)-haloalkyl,     -   where the above-mentioned radicals R² are substituted by s         radicals from the group consisting of cyano, halogen, nitro and         s represents 0, 1, 2 or 3,         with the proviso that the compounds

-   3-amino-4-bromo-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,

-   4-bromo-2,6-difluoro-2-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,

-   3-amino-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,

-   2,6-difluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3 nitrobenzamide, and

-   3-amino-2,6-difluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide     are excluded.

A particular aspect of the invention relates to N-(1,3,4-oxadiazol-2-yl)arylcarboxamides of the formula (I) in which the substituents have the following meaning:

A represents C—Y,

R represents hydrogen, methyl, ethyl, trifluoromethyl or methoxymethyl,

X represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl or cyclopropyl,

Y represents S(O)_(n)R²,

Z represents trifluoromethyl, difluoromethyl or pentafluoroethyl,

V represents hydrogen,

W represents fluorine and

R² represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,

-   -   where the above-mentioned radicals R² are substituted by s         radicals from the group consisting of cyano, halogen, nitro,         n represents 0, 1 or 2,         s represents 0, 1,2 or 3.

With respect to the generically defined substituent Y═S(O)_(n)R² where n=0, n=1 or n=2, most preference is given to the radicals methylsulfanyl (SMe), methylsulfinyl (methyl sulfoxide (SOMe)), methylsulfonyl (SO₂Me), ethylsulfanyl (SEt), ethylsulfinyl (ethyl sulfoxide (SOEt)) and ethylsulfonyl (SO₂Et) where R²=methyl (Me) or R²=ethyl (Et).

Utmost preference is given to the three methyl-substituted alternatives of Y, i.e. Y═SMe, Y═SOMe, Y═SO₂Me.

Accordingly, N-(1,3,4-oxadiazol-2-yl)arylcarboxamides of the formula (I) in which the substituents have the following meaning:

A represents C—Y,

R represents methyl,

X represents chlorine or methyl,

Y represents SMe, SOMe or SO₂Me,

Z represents trifluoromethyl or chlorine,

V represents hydrogen,

W represents fluorine,

are particularly preferred in the context of the particular aspect mentioned above.

The following tabular compilation specifically discloses six of the compounds of the general formula (I) which are most preferred according to the aspect mentioned above in which, as shown in the formula below, A represents CY, X represents chlorine or methyl, Y represents methylsulfanyl, methylsulfinyl or methylsulfonyl, Z represents trifluoromethyl, V represents hydrogen, W represents fluorine and R represents methyl:

No. X Y Compound 2-143 Cl SMe 2-chloro-6-fluoro-N-(5-methyl-1,3,4- oxadiazol-2-yl)-3-(methylsulfanyl)-4- (trifluoromethyl)benzamide 2-144 Cl S(O)Me 2-chloro-6-fluoro-N-(5-methyl-1,3,4- oxadiazol-2-yl)-3-(methylsulfinyl)-4- (trifluoromethyl)benzamide 2-145 Cl SO₂Me 2-chloro-6-fluoro-N-(5-methyl-1,3,4- oxadiazol-2-yl)-3-(methylsulfonyl)-4- (trifluoromethyl)benzamide 2-359 Me SMe 6-fluoro-2-methyl-N-(5-methyl-1,3,4- oxadiazol-2-yl)-3-(methylsulfanyl)-4- (trifluoromethyl)benzamide 2-360 Me S(O)Me 6-fluoro-2-methyl-N-(5-methyl-1,3,4- oxadiazol-2-yl)-3-(methylsulfinyl)-4- (trifluoromethyl)benzamide 2-361 Me SO₂Me 6-fluoro-2-methyl-N-(5-methyl-1,3,4- oxadiazol-2-yl)-3-(methylsulfonyl)-4- (trifluoromethyl)benzamide

Moreover, preference is given to N-(1,3,4-oxadiazol-2-yl)arylcarboxamides of the formula (I) in which A represents C—Y, where

R represents hydrogen, methyl, ethyl, trifluoromethyl or methoxymethyl,

X represents F, Cl, Br, CH₃, ethyl, n-propyl, isopropyl, CF₃, O—CH₂-cyclopropyl, SMe or SO₂Me,

Y represents H, F, Cl, Me, ethyl, propyl, isopropyl, CH₂OMe, CH₂OEt, CH₂OCH₂CHF₂, CH₂OCH₂CF₃,

-   -   CH₂OCH₂CF₂CHF₂, CH₂O-c-pentyl, CH₂O-tetrahydrofuran-3-yl,         CH₂OCH₂-tetrahydrofuran-2-yl, CH₂OCH₂-tetrahydrofuran-3-yl,         CH₂PO(OMe)₂, COOMe, CONMe₂, CONMe(OMe), NH₂, NHMe, NMe₂, NHEt,         NH(CH₂)₂OMe, NH(CH₂)₂OEt, OH, OMe, OEt, OiPr, O(CH₂)₂OMe,         O(CH₂)₃OMe, O(CH₂)₄OMe, OCH₂CHF₂, OCH₂(CO)NMe₂,         O(CH₂)₂—(CO)—NMe₂, O(CH₂)₂—NH(CO)NMe₂, O(CH₂)₂—NH(CO)NHCO₂Et,         O(CH₂)₂—NHCO₂Me, O(CH₂)₂—NHSO₂Me, OCH₂—NHSO₂cPr, O(CH₂)₂NHSO₂Me,         O(CH₂)-5-2,4-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one,         O(CH₂)-3,5-dimethyl-1,2-oxazol-4-yl, O(CH₂)-5-pyrrolidin-2-one,         O(CH₂)₂—O(3,5-di-methoxypyrimidin-2-yl, SMe, SEt, S(CH₂)₂OMe,         SO(CH₂)₂OMe, SO₂(CH₂)₂OMe, S(O)Me, S(O)Et, SO₂Me, SO₂Et,         SO₂(CH₂)₂OMe,

-   4,5-dihydro-1,2-oxazol-3 yl,     5-cyanomethyl-4,5-dihydro-1,2-oxazol-3-yl, [1,4]dioxan-2-ylmethoxy,     pyrazol-1-yl, 4-methoxylpyrazol-1-yl, 1,2,3-triazol-1-yl,     5-(methoxymethyl)-4,5-dihydro-1,2-oxazol-3-yl or

-   5-cyanomethyl-4,5-dihydro-1,2-oxazol-3-yl and     Z represents F, Cl, Br, I, CF₃, NO₂, SMe, SEt, SOMe, SOEt, SO₂Me,     SO₂Et, pyrazol-1-yl or 1H-1,2,4-triazol-1-yl,     with the proviso that the compounds

-   3-amino-4-bromo-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,     and also

-   4-bromo-2,6-difluoro-2-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,     are excluded.

Alternatively, preference is given to N-(1,3,4-oxadiazol-2-yl)arylcarboxamides of the formula (I) in which A represents N (instead of C—Y), where

V represents hydrogen,

W represents fluorine,

Z represents CF₃,

and the radicals

R, X and Y as well as the radicals R¹ to R² and also m, n and s are each independently of one another as defined above.

In all the formulae specified hereinafter, the substituents and symbols have the same meaning as described in formula (I), unless defined differently.

Compounds according to the invention can be prepared, for example, by the method shown in scheme 1, by base-catalyzed reaction of a benzoyl or nicotinoyl chloride (II) with a 2-amino-1,3,4-oxadiazole (III):

The benzoyl chlorides of the formula (II) or the parent benzoic acids thereof are known in principle and can be prepared, for example, by the methods described in U.S. Pat. No. 6,376,429 B1, EP 1 585 742 A1, WO2014/184015, WO2014/184016, WO2013/083859 and EP 1202 978 A1.

Compounds according to the invention can also be prepared by the method described in scheme 2, by reacting a benzoic or nicotinic acid of the formula (IV) with a 2-amino-1,3,4-oxadiazole (III):

For the activation, it is possible to use dehydrating reagents which are typically used for amidation reactions, for example 1,1′-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC), 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P), etc.

Inventive compounds can also be prepared by the method described in scheme 3, by cyclizing a compound of the formula V:

The cyclization can be performed by the methods described in Synth. Commun. 31 (12), 1907-1912 (2001) or in Indian J. Chem., Section B: Organic Chemistry Including Medicinal Chemistry; Vol. 43 (10), 2170-2174 (2004).

The compound of the formula V used in scheme 3 can be prepared by reaction of an acyl isocyanate of the formula VII with a hydrazide of the formula VI by the method described in Synth. Commun. 25(12), 1885-1892 (1995).

It may be appropriate to alter the sequence of the reaction steps. For instance, benzoic acids bearing a sulfoxide cannot be converted directly to their acid chlorides. One option here is first to prepare the amide at the thioether stage, and then to oxidize the thioether to the sulfoxide.

Collections of compounds of the formula (I) and/or salts thereof which can be synthesized by the abovementioned reactions can also be prepared in a parallelized manner, in which case this may be accomplished in a manual, partly automated or fully automated manner. It is possible, for example, to automate the conduct of the reaction, the workup or the purification of the products and/or intermediates. Overall, this is understood to mean a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry—Synthesis, Analysis, Screening (editor: Gunther Jung), Wiley, 1999, on pages 1 to 34.

For the parallelized conduct of the reaction and workup, it is possible to use a number of commercially available instruments, for example Calypso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB113AZ, England, or MultiPROBE Automated Workstations from Perkin Elmer, Waltham, Mass. 02451, USA. For the parallelized purification of compounds of the general formula (I) and salts thereof or of intermediates which occur in the course of preparation, available apparatuses include chromatography apparatuses, for example from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.

The apparatuses detailed lead to a modular procedure in which the individual working steps are automated, but manual operations have to be carried out between the working steps. This can be circumvented by using partly or fully integrated automation systems in which the respective automation modules are operated, for example, by robots. Automation systems of this type can be obtained, for example, from Caliper, Hopkinton, Mass. 01748, USA.

The implementation of single or multiple synthesis steps can be supported by the use of polymer-supported reagents/scavenger resins. The specialist literature describes a series of experimental protocols, for example in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).

Aside from the methods described here, compounds of the general formula (I) and salts thereof can be prepared completely or partially by solid-phase-supported methods. For this purpose, individual intermediates or all intermediates in the synthesis or a synthesis adapted for the corresponding procedure are bound to a synthesis resin. Solid-phase-supported synthesis methods are described adequately in the technical literature, for example Barry A. Bunin in “The Combinatorial Index”, Academic Press, 1998 and Combinatorial Chemistry—Synthesis, Analysis, Screening (editor: Gunther Jung), Wiley, 1999. The use of solid-phase-supported synthesis methods permits a number of protocols, which are known from the literature and which for their part may be performed manually or in an automated manner. The reactions can be performed, for example, by means of IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, Calif. 92064, USA.

Both in the solid and in the liquid phase, the implementation of individual or several synthesis steps may be supported by the use of microwave technology. The specialist literature describes a series of experimental protocols, for example in Microwaves in Organic and Medicinal Chemistry (editors: C. O. Kappe and A. Stadler), Wiley, 2005.

The preparation by the processes described here gives compounds of the formula (I) and salts thereof in the form of substance collections, which are called libraries. The present invention also provides libraries comprising at least two compounds of the formula (I) and salts thereof.

The compounds of the formula (I) according to the invention (and/or salts thereof), referred to collectively as “compounds according to the invention” hereinafter, have excellent herbicidal efficacy against a broad spectrum of economically important monocotyledonous and dicotyledonous annual harmful plants. The active ingredients also have good control over perennial harmful plants which are difficult to control and produce shoots from rhizomes, root stocks or other perennial organs.

The present invention therefore also provides a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, in which one or more compound(s) of the invention is/are applied to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds or unwanted crop plants), the seed (for example grains, seeds or vegetative propagules such as tubers or shoot parts with buds) or the area on which the plants grow (for example the area under cultivation). The compounds of the invention can be deployed, for example, prior to sowing (if appropriate also by incorporation into the soil), prior to emergence or after emergence. Specific examples of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds of the invention are as follows, though the enumeration is not intended to impose a restriction to particular species.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

If the compounds of the invention are applied to the soil surface before germination, either the emergence of the weed seedlings is prevented completely or the weeds grow until they have reached the cotyledon stage, but then they stop growing and ultimately die completely after three to four weeks have passed.

If the active compounds are applied post-emergence to the green parts of the plants, growth stops after the treatment, and the harmful plants remain at the growth stage at the time of application, or they die completely after a certain time, so that in this manner competition by the weeds, which is harmful to the crop plants, is eliminated very early and in a sustained manner.

Although the compounds of the invention have outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, will be damaged to a negligible extent only, if at all, depending on the structure of the particular compound of the invention and its application rate. For these reasons, the present compounds are very suitable for selective control of unwanted plant growth in plant crops such as agriculturally useful plants or ornamental plants.

In addition, the compounds of the invention (depending on their particular structure and the application rate deployed) have outstanding growth-regulating properties in crop plants. They intervene in the plants' own metabolism with regulatory effect, and can thus be used for the controlled influencing of plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth without killing the plants in the process. Inhibition of vegetative growth plays a major role for many mono- and dicotyledonous crops since, for example, this can reduce or completely prevent lodging.

By virtue of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material.

It is preferable, with respect to transgenic crops, to use the compounds of the invention in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet/sorghum, rice and corn or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other types of vegetable. Preferably, the compounds of the invention can be used as herbicides in crops of useful plants which are resistant, or have been made resistant by genetic engineering, to the phytotoxic effects of the herbicides.

Preference is given to the use of the compounds according to the invention or salts thereof in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet/sorghum, rice, cassava and corn, or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other types of vegetable. Preferably, the compounds of the invention can be used as herbicides in crops of useful plants which are resistant, or have been made resistant by genetic engineering, to the phytotoxic effects of the herbicides.

Conventional ways of producing novel plants which have modified properties in comparison to existing plants consist, for example, in traditional cultivation methods and the generation of mutants.

Alternatively, novel plants with modified properties can be generated with the aid of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, there have been descriptions in several cases of:

-   -   genetic modifications of crop plants for the purpose of         modifying the starch synthesized in the plants (e.g. WO         92/11376, WO 92/14827, WO 91/19806),     -   transgenic crop plants which are resistant to particular         herbicides of the glufosinate type (cf., for example,         EP-A-0242236, EP-A-242246) or glyphosate type (WO 92/00377) or         the sulfonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659),     -   transgenic crop plants, for example cotton, capable of producing         Bacillus thuringiensis toxins (Bt toxins), which make the plants         resistant to particular pests (EP-A-0142924, EP-A-0193259).     -   transgenic crop plants having a modified fatty acid composition         (WO 91/13972),     -   genetically modified crop plants with novel constituents or         secondary metabolites, for example novel phytoalexins, which         bring about an increased disease resistance (EPA 309862,         EPA0464461),     -   genetically modified plants having reduced photorespiration,         which have higher yields and higher stress tolerance (EPA         0305398),     -   transgenic crop plants which produce pharmaceutically or         diagnostically important proteins (“molecular pharming”),     -   transgenic crop plants which feature higher yields or better         quality,     -   transgenic crop plants which feature a combination, for example,         of the abovementioned novel properties (“gene stacking”).

Numerous molecular biology techniques which can be used to produce novel transgenic plants with modified properties are known in principle; see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, “Trends in Plant Science” 1 (1996) 423-431.

For such genetic manipulations, nucleic acid molecules which allow mutagenesis or sequence alteration by recombination of DNA sequences can be introduced into plasmids. With the aid of standard methods, it is possible, for example, to undertake base exchanges, remove parts of sequences or add natural or synthetic sequences. To join the DNA fragments with one another, adapters or linkers can be placed onto the fragments, see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y., or Winnacker “Gene und Klone” [Genes and clones], VCH Weinheim 2nd edition 1996.

For example, the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect, or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product. To this end, it is firstly possible to use DNA molecules which encompass the entire coding sequence of a gene product inclusive of any flanking sequences which may be present, and also DNA molecules which only encompass portions of the coding sequence, in which case it is necessary for these portions to be long enough to have an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical to them.

When expressing nucleic acid molecules in plants, the protein synthesized may be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to join the coding region to DNA sequences which ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). The nucleic acid molecules can also be expressed in the organelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques to give rise to entire plants. In principle, the transgenic plants may be plants of any desired plant species, i.e. not only monocotyledonous but also dicotyledonous plants.

Thus, transgenic plants can be obtained whose properties are altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.

The compounds of the invention can be used with preference in transgenic crops which are resistant to growth regulators, for example dicamba, or to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of the sulfonylureas, the glyphosates, glufosinates or benzoylisoxazoles and analogous active compounds.

When the active compounds of the invention are employed in transgenic crops, not only do the effects towards harmful plants observed in other crops occur, but frequently also effects which are specific to the application in the particular transgenic crop, for example an altered or specifically widened spectrum of weeds which can be controlled, altered application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.

The invention therefore also provides for the use of the compounds of the invention as herbicides for control of harmful plants in transgenic crop plants.

The compounds of the invention can be applied in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in the customary formulations. The invention therefore also provides herbicidal and plant-growth-regulating compositions which comprise the compounds of the invention.

The compounds of the invention can be formulated in various ways, according to the biological and/or physicochemical parameters required. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for scattering and soil application, granules (GR) in the form of microgranules, spray granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hanser Verlag Munich, 4th Ed. 1986, Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973, K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries required, such as inert materials, surfactants, solvents and further additives, are likewise known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”, 2nd Ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie” [Chemical Engineering], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

On the basis of these formulations, it is also possible to produce combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides, fungicides, and also with safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or as a tank mix. Suitable safeners are, for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and dichlormid.

Wettable powders are preparations uniformly dispersible in water which, alongside the active ingredient apart from a diluent or inert substance, also comprise surfactants of an ionic and/or non-ionic type (wetting agent, dispersant), e.g. polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol poly glycolethersulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. To produce the wettable powders, the herbicidally active compounds are finely ground, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.

Emulsifiable concentrates are produced by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

Dusting products are obtained by grinding the active compound with finely distributed solids, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Suspension concentrates may be water- or oil-based. They may be prepared, for example, by wet-grinding by means of commercial bead mills and optional addition of surfactants as have, for example, already been listed above for the other formulation types. Emulsions, for example oil-in-water emulsions (EW), can be produced, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants as already listed above, for example, for the other formulation types. Granules can be produced either by spraying the active compound onto adsorptive granular inert material or by applying active compound concentrates to the surface of carriers, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active compounds can also be granulated in the manner customary for the production of fertilizer granules—if desired as a mixture with fertilizers. Water-dispersible granules are produced generally by the customary processes such as spray-drying, fluidized-bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material. For the production of pan, fluidized-bed, extruder and spray granules, see e.g. processes in “Spray-Drying Handbook” 3rd Ed. 1979, G. Goodwin Ltd., London, J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff.; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57. For further details regarding the formulation of crop protection compositions, see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

The agrochemical preparations contain generally 0.1 to 99% by weight, especially 0.1 to 95% by weight, of compounds of the invention.

In wettable powders, the active compound concentration is, for example, about 10 to 90% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates, the active compound concentration may be about 1% to 90% and preferably 5% to 80% by weight. Dust-type formulations contain

1% to 30% by weight of active ingredient, preferably usually 5% to 20% by weight of active ingredient; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of active ingredient. In the case of water-dispersible granules, the active compound content depends partially on whether the active compound is in liquid or solid form and on which granulation auxiliaries, fillers, etc., are used. In the water-dispersible granules, the content of active compound is, for example, between 1% and 95% by weight, preferably between 10% and 80% by weight.

In addition, the active compound formulations mentioned optionally comprise the respective customary stickers, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and the viscosity.

On the basis of these formulations, it is also possible to produce combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides, fungicides, and also with safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or as a tank mix.

Active compounds which can be employed in combination with the compounds according to the invention in mixed formulations or in the tank mix are, for example, known active compounds which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as are described in, for example, Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 15th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2009 and the literature cited therein. Examples of known herbicides or plant growth regulators which can be combined with the inventive compounds include the active ingredients which follow (the compounds are designated by the common name according to the International Organization for Standardization (ISO) or by the chemical name or by the code number) and always encompass all use forms, such as acids, salts, esters and isomers, such as stereoisomers and optical isomers. These include, by way of example, one use form and in some cases also a plurality of use forms:

acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryne, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminopyralid, amitrole, ammonium sulfamate, ancymidol, anilofos, asulam, atrazine, azafenidin, azimsulfuron, aziprotryne, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bensulfuron, bensulfuron-methyl, bentazone, benzfendizone, benzobicyclon, benzofenap, benzofluor, benzoylprop, bicyclopyrone, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromuron, buminafos, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorazifop, chlorazifop-butyl, chlorbromuron, chlorbufam, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat-chloride, chlornitrofen, chlorophthalim, chlorthal-dimethyl, chlorotoluron, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clethodim, clodinafop, clodinafop-propargyl, clofencet, clomazone, clomeprop, cloprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cyclanilide, cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, 2,4-D, 2,4-DB, daimuron/dymron, dalapon, daminozide, dazomet, n-decanol, desmedipham, desmetryn, detosyl-pyrazolate (DTP), diallate, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, diethatyl, diethatyl-ethyl, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dikegulac-sodium, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimetrasulfuron, dinitramine, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, diquat-dibromide, dithiopyr, diuron, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethephon, ethidimuron, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5331, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fentrazamide, fenuron, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, flupoxam, flupropacil, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen, foramsulfuron, forchlorfenuron, fosamine, furyloxyfen, gibberellic acid, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-isopropylammonium, H-9201, i.e. 0-(2,4-dimethyl-6-nitrophenyl)O-ethyl isopropylphosphoramidothioate, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, inabenfide, indanofan, indaziflam, indoleacetic acid (IAA), 4-indol-3-ylbutyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ipfencarbazone, isocarbamid, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, karbutilate, 1H, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide, mepiquat-chloride, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazasulfuron, methazole, methiopyrsulfuron, methiozolin, methoxyphenone, methyldymron, 1-methylcyclopropene, methyl isothiocyanate, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monocarbamide, monocarbamide dihydrogensulfate, monolinuron, monosulfuron, monosulfuron esters, monuron, MT-128, i.e. 6-chloro-N-[(2E)-3-chloroprop-2-en-1-yl]-5-methyl-N-phenylpyridazine-3-amine, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, naproanilide, napropamide, naptalam, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrophenolate-sodium (isomer mixture), nitrofluorfen, nonanoic acid, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paclobutrazole, paraquat, paraquat dichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, picloram, picolinafen, pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor, primisulfuron, primisulfuron-methyl, probenazole, profluazol, procyazine, prodiamine, prifluraline, profoxydim, prohexadione, prohexadione-calcium, prohydrojasmone, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, prynachlor, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, secbumeton, sethoxydim, siduron, simazine, simetryn, SN-106279, i.e. methyl (2R)-2-({7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthyl} oxy)propanoate, sulcotrione, sulfallate (CDEC), sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosate (glyphosate-trimesium), sulfosulfuron, SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chlor-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryne, thenylchlor, thiafluamide, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiocarbazil, topramezone, tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, trimeturon, trinexapac, trinexapac-ethyl, tritosulfuron, tsitodef, uniconazole, uniconazole-P, vernolate, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds

For application, the formulations in commercial form are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules with water. Dust-type preparations, granules for soil application or granules for scattering and sprayable solutions are not normally diluted further with other inert substances prior to application.

The required application rate of the compounds of the formula (I) varies with the external conditions, including, inter alia, temperature, humidity and the type of herbicide used. It can vary within wide limits, for example between 0.001 and 1.0 kg/ha or more of active substance, but it is preferably between 0.005 and 750 g/ha.

The examples which follow illustrate the invention.

A. CHEMICAL EXAMPLES Preparation of 2,4-dichloro-6-fluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(methylsulfanyl)benzamide Ex. No. 2-242

-   -   1. Preparation of         1,3-dichloro-5-fluoro-2-(methylsulfanyl)benzene         -   Under an atmosphere of nitrogen and at 0° C., 9.5 g (67             mmol) of methyl iodide are added to a mixture of 11.0 g             (55.8 mmol) of 2,6-dichloro-4-fluorobenzenethiol and 11.6 g             (84 mmol) of K2CO3 in 50 ml of DMF. After 12 h of stirring             at room temperature, the reaction mixture is poured onto ice             and then extracted with tert-butyl methyl ether. The organic             phase is washed twice with water and once with sat. NaCl             solution, dried over sodium sulfate and concentrated. Yield:             10.55 g (90%); slightly yellowish oil.     -   2. Preparation of         2,4-dichloro-6-fluoro-3-(methylsulfanyl)benzoic acid         -   At −78° C., 20 ml (50 mmol) of a 2.5 M nBuLi solution are             added dropwise to a solution of 10.55 g (50 mmol) of             1,3-dichloro-5-fluoro-2-(methylsulfanyl)benzoline in 100 ml             of THF (abs.). After 1 h of stirring at −78° C., an excess             of CO₂ is passed through. The reaction mixture is             subsequently allowed to warm to room temperature and then             poured into 500 ml of a 1 M aqueous sodium hydroxide             solution. The mixture is then washed with t-butyl methyl             ether. The aqueous phase is acidified to pH 4 using a 2 M             HCl solution and then extracted with t-butyl methyl ether.             The organic phase is dried over sodium sulfate, filtered and             concentrated. Yield: 10 g (39 mmol; 78%). ¹H-NMR (40 MHz;             DMSO-d₆): 7.63 ppm (d, 1H); 2.42 (s, 3H).     -   3.         2,4-Dichloro-6-fluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(methylsulfanyl)benzamide         (Ex. No. 2-242)         -   At 0° C., 448 mg (0.309 ml, 3.53 mmol) of oxalyl chloride             are added dropwise to a solution of 600 mg (2.35 mmol) of             2,4-dichloro-6-fluoro-3-(methylsulfanyl)benzoic acid and 326             mg (3.29 mmol) of 2-amino-5-methyl-1,3,4-oxadiazole in 20 ml             of pyridine. After 1 h at 0° C., the reaction mixture is             warmed to room temperature and stirred at room temperature             for 14 h. The mixture is then concentrated and 20 ml each of             dichloromethane and water are added to the residue. After             separation of the phases, the organic phase is dried over             sodium sulfate, filtered and concentrated. The residue is             purified by column chromatography (silica gel, heptane/ethyl             acetate).

Yield: 165 mg (90% pure; 19%) 1H-NMR (40 MHz; DMSO-d⁶): 12.59 ppm (bs, 1H), 7.86 ppm (d, 1H); 2.41 ppm (s, 3H).

Preparation of 2,4-dichloro-6-fluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(methylsulfinyl)benzamide Ex. No. 2-243

-   -   At 0° C., 107 mg (0.465 mmol) meta-chloroperbenzoic acid are         added to a solution of 115 mg (0.274 mmol) of         2,4-dichloro-6-fluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(methylsulfanyl)benzamide         (Ex. No. 2-242) in 20 ml of dichloromethane. After 2 days of         stirring at room temperature, an aqueous bisulfite solution is         added. Following extraction, the organic phase is concentrated         and purified by column chromatography (HPLC;         acetonitrile/water).

Yield: 32 mg (95% pure; 31%) H-NMR (40 MHz; DMSO-d₆): 11.60 ppm (bs, 1H), 7.24 ppm (d, 1H); 3.07 ppm (s, 3H).

The abbreviations used mean:

Et = ethyl Me = methyl n-Pr = n-propyl i-Pr = isopropyl c-Pr = cyclopropyl Ph = phenyl Ac = acetyl Bz = benzoyl

TABLE 1 Compounds of the general formula (I) in which A represents CY, W represents fluorine and V and R represent hydrogen

Physical data (¹H-NMR, DMSO-d₆, No. X Y Z 400 MHz) 1-1 F H Cl 1-2 F H SO₂Me 1-3 F H SO₂Et 1-4 F H CF₃ 1-5 F H NO₂ 1-6 Cl H Br 1-7 Cl H SMe 1-8 Cl H SOMe 1-9 Cl H SO₂Me 1-10 Cl H SO₂CH₂Cl 1-11 Cl H SEt 1-12 Cl H SO₂Et 1-13 Cl H CF₃ 1-14 Cl H NO₂ 1-15 Cl H pyrazol-1-yl 1-16 Cl H 1H-1,2,4- triazol-1-yl 1-17 Br H Cl 1-18 Br H Br 1-19 Br H SO₂Me 1-20 Br H SO₂Et 1-21 Br H CF₃ 1-22 SO₂Me H Cl 1-23 SO₂Me H Br 1-24 SO₂Me H SMe 1-25 SO₂Me H SOMe 1-26 SO₂Me H SO₂Me 1-27 SO₂Me H SO₂Et 1-28 SO₂Me H CF₃ 1-29 SO₂Et H Cl 1-30 SO₂Et H Br 1-31 SO₂Et H SMe 1-32 SO₂Et H SOMe 1-33 SO₂Et H SO₂Me 1-34 SO₂Et H CF₃ 1-35 NO₂ H F 1-36 NO₂ H Cl 1-37 NO₂ H Br 1-38 NO₂ H I 1-39 NO₂ H CN 1-40 NO₂ H SO₂Me 1-41 NO₂ H SO₂Et 1-42 NO₂ H CF₃ 1-43 Me H Cl 1-44 Me H Br 1-45 Me H SMe 1-46 Me H SO₂Me 1-47 Me H SO₂CH₂Cl 1-48 Me H SEt 1-49 Me H SO₂Et 1-50 Me H CF₃ 1-51 CH₂SO₂Me H CF₃ 1-52 Et H Cl 1-53 Et H Br 1-54 Et H SMe 1-55 Et H SO₂Me 1-56 Et H SO₂CH₂Cl 1-57 Et H SEt 1-58 Et H SO₂Et 1-59 Et H CF₃ 1-60 CF₃ H Cl 1-61 CF₃ H Br 1-62 CF₃ H SO₂Me 1-63 CF₃ H SO₂Et 1-64 CF₃ H CF₃ 1-65 NO₂ NH₂ F 1-66 NO₂ NHMe F 1-67 NO₂ NMe₂ F 1-68 NO₂ Me Cl 1-69 NO₂ NH₂ Cl 1-70 NO₂ NHMe Cl 1-71 NO₂ NMe₂ Cl 1-72 NO₂ NH₂ Br 1-73 NO₂ NHMe Br 1-74 NO₂ NMe₂ Br 1-75 NO₂ NH₂ CF₃ 1-76 NO₂ NMe₂ CF₃ 1-77 NO₂ NH₂ SO₂Me 1-78 NO₂ NH₂ SO₂Et 1-79 NO₂ NHMe SO₂Me 1-80 NO₂ NMe₂ SO₂Me 1-81 NO₂ NMe₂ SO₂Et 1-82 NO₂ NH₂ 1H-1,2,4-triazol-1-yl 1-83 NO₂ NHMe 1H-1,2,4-triazol-1-yl 1-84 NO₂ NMe₂ 1H-1,2,4-triazol-1-yl 1-85 Me SMe H 1-86 Me SOMe H 1-87 Me SO₂Me H 1-88 Me SEt H 1-89 Me SOEt H 1-90 Me SO₂Et H 1-91 Me S(CH₂)₂OMe H 1-92 Me SO(CH₂)₂OMe H 1-93 Me SO₂(CH₂)₂OMe H 1-94 Me F F 1-95 Me F Cl 1-96 Me SEt F 1-97 Me SOEt F 1-98 Me SO₂Et F 1-99 Me Me Cl 1-100 Me F Cl 1-101 Me Cl Cl 1-102 Me NH₂ Cl 1-103 Me NHMe Cl 1-104 Me NMe₂ Cl 1-105 Me O(CH₂)₂OMe Cl 1-106 Me O(CH₂)₃OMe Cl 1-107 Me O(CH₂)₄OMe Cl 1-108 Me OCH₂CONMe₂ Cl 1-109 Me O(CH₂)₂—CO—NMe₂ Cl 1-110 Me O(CH₂)₂—NH(CO)NMe₂ Cl 1-111 Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 1-112 Me O(CH₂)₂—NHCO₂Me Cl 1-113 Me OCH₂—NHSO₂cPr Cl 1-114 Me O(CH₂)-5-2,4- Cl dimethyl-2,4- dihydro-3H-1,2,4- triazol-3-one 1-115 Me O(CH₂)-3,5- Cl dimethyl-1,2- oxazol-4-yl 1-116 Me SMe Cl 1-117 Me SOMe Cl 1-118 Me SO₂Me Cl 1-119 Me SEt Cl 1-120 Me SOEt Cl 1-121 Me SO₂Et Cl 1-122 Me S(CH₂)₂OMe Cl 1-123 Me SO(CH₂)₂OMe Cl 1-124 Me SO₂(CH₂)₂OMe Cl 1-125 Me NH₂ Br 1-126 Me NHMe Br 1-127 Me NMe₂ Br 1-128 Me OCH₂(CO)NMe₂ Br 1-129 Me O(CH₂)-5- Br pyrrolidin-2-one 1-130 Me SMe Br 1-131 Me SOMe Br 1-132 Me SO₂Me Br 1-133 Me SEt Br 1-134 Me SOEt Br 1-135 Me SO₂Et Br 1-136 Me SMe I 1-137 Me SOMe I 1-138 Me SO₂Me I 1-139 Me SEt I 1-140 Me SOEt I 1-141 Me SO₂Et I 1-142 Me Cl CF₃ 1-143 Me SMe CF₃ 1-144 Me SOMe CF₃ 1-145 Me SO₂Me CF₃ 1-146 Me SEt CF₃ 1-147 Me SOEt CF₃ 1-148 Me SO₂Et CF₃ 1-149 Me S(CH₂)₂OMe CF₃ 1-150 Me SO(CH₂)₂OMe CF₃ 1-151 Me SO₂(CH₂)₂OMe CF₃ 1-152 Me Me SO₂Me 1-153 Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 1-154 Me 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 1-155 Me 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol- 3-yl 1-156 Me 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 1-157 Me NH₂ SO₂Me 1-158 Me NHMe SO₂Me 1-159 Me NMe₂ SO₂Me 1-160 Me NH(CH₂)₂OMe SO₂Me 1-161 Me pyrazol-1-yl SO₂Me 1-162 Me OH SO₂Me 1-163 Me OMe SO₂Me 1-164 Me OMe SO₂Et 1-165 Me OEt SO₂Me 1-166 Me OEt SO₂Et 1-167 Me OiPr SO₂Me 1-168 Me OiPr SO₂Et 1-169 Me O(CH₂)₂OMe SO₂Me 1-170 Me O(CH₂)₂OMe SO₂Et 1-171 Me O(CH₂)₃OMe SO₂Me 1-172 Me O(CH₂)₃OMe SO₂Et 1-173 Me O(CH₂)₄OMe SO₂Me 1-174 Me O(CH₂)₄OMe SO₂Et 1-175 Me O(CH₂)₂NHSO2Me SO₂Me 1-176 Me O(CH₂)₂NHSO2Me SO₂Et 1-177 Me OCH₂(CO)NMe₂ SO₂Me 1-178 Me OCH₂(CO)NMe₂ SO₂Et 1-179 Me [1,4]dioxan-2- SO₂Me ylmethoxy 1-180 Me [1,4]dioxan-2- SO₂Et ylmethoxy 1-181 Me O(CH₂)₂—O-(3,5- SO₂Me dimethoxypyrimidin- 2-yl) 1-182 Me Cl SO₂Me 1-183 Me SMe SO₂Me 1-184 Me SOMe SO₂Me 1-185 Me SO₂Me SO₂Me 1-186 Me SO₂Me SO₂Et 1-187 Me SEt SO₂Me 1-188 Me SOEt SO₂Me 1-189 Me SO₂Et SO₂Me 1-190 Me S(CH₂)₂OMe SO₂Me 1-191 Me SO(CH₂)₂OMe SO₂Me 1-192 Me SO₂(CH₂)₂OMe SO2Me 1-193 CH₂SMe OMe SO₂Me 1-194 CH₂OMe OMe SO₂Me 1-195 CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 1-196 CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂Me 1-197 CH₂O(CH₂)₃OMe OMe SO₂Me 1-198 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me 1-199 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 1-200 Et SMe Cl 1-201 Et SO₂Me Cl 1-202 Et SMe CF₃ 1-203 Et SO₂Me CF₃ 1-204 Et F SO₂Me 1-205 Et NH(CH₂)₂OMe SO₂Me 1-206 iPr SO₂Me CF₃ 1-207 cPr SO₂Me CF₃ 1-208 CF₃ O(CH₂)₂OMe F 1-209 CF₃ O(CH₂)₃OMe F 1-210 CF₃ OCH₂CONMe₂ F 1-211 CF₃ [1,4]dioxan-2- F ylmethoxy 1-212 CF₃ O(CH₂)₂OMe Cl 1-213 CF₃ O(CH₂)₃OMe Cl 1-214 CF₃ OCH₂CONMe₂ Cl 1-215 CF₃ [1,4]dioxan-2- Cl ylmethoxy 1-216 CF₃ O(CH₂)₂OMe Br 1-217 CF₃ O(CH₂)₃OMe Br 1-218 CF₃ OCH₂CONMe₂ Br 1-219 CF₃ [1,4]dioxan-2- Br ylmethoxy 1-220 CF₃ O(CH₂)₂OMe I 1-221 CF₃ O(CH₂)₃OMe I 1-222 CF₃ OCH₂CONMe₂ I 1-223 CF₃ [1,4]dioxan-2- I ylmethoxy 1-224 CF₃ F SO₂Me 1-225 CF₃ F SO₂Et 1-226 CF₃ O(CH₂)₂OMe SO₂Me 1-227 CF₃ O(CH₂)₂OMe SO₂Et 1-228 CF₃ O(CH₂)₃OMe SO₂Me 1-229 CF₃ O(CH₂)₃OMe SO₂Et 1-230 CF₃ OCH₂CONMe₂ SO₂Me 1-231 CF₃ OCH₂CONMe₂ SO₂Et 1-232 CF₃ [1,4]dioxan-2- SO₂Me ylmethoxy 1-233 CF₃ [1,4]dioxan-2- SO₂Et ylmethoxy 1-234 F SMe CF₃ 1-235 F SOMe CF₃ 1-236 Cl Me Cl 1-237 Cl OCH₂CHCH₂ Cl 1-238 Cl OCH₂CHF₂ Cl 1-239 Cl O(CH₂)₂OMe Cl 1-240 Cl OCH₂CONMe₂ Cl 1-241 Cl O(CH₂)-5- Cl pyrrolidin-2-one 1-242 Cl SMe Cl 1-243 Cl SOMe Cl 1-244 Cl SO₂Me Cl 1-245 Cl F SMe 1-246 Cl Cl SO₂Me 1-247 Cl COOMe SO₂Me 1-248 Cl CONMe₂ SO₂Me 1-249 Cl CONMe(OMe) SO₂Me 1-250 Cl CH₂OMe SO₂Me 1-251 Cl CH₂OMe SO₂Et 1-252 Cl CH₂OEt SO₂Me 1-253 Cl CH₂OEt SO₂Et 1-254 Cl CH₂OCH₂CHF₂ SO₂Me 1-255 Cl CH₂OCH₂CF₃ SO₂Me 1-256 Cl CH₂OCH₂CF₃ SO₂Et 1-257 Cl CH₂OCH₂CF₂CHF₂ SO₂Me 1-258 Cl CH₂O-c-pentyl SO₂Me 1-259 Cl CH₂PO(OMe)₂ SO₂Me 1-260 Cl 4,5-dihydro-1,2- SMe oxazol-3-yl 1-261 Cl 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 1-262 Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 1-263 Cl 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol- 3-yl 1-264 Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 1-265 Cl 5- SO₂Et (methoxymethyl)- 4,5-dihydro-1,2- oxazol-3-yl 1-266 Cl 5- SO₂Et (methoxymethyl)- 5-methyl-4,5- dihydro-1,2- oxazol-3-yl 1-267 Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 1-268 Cl CH₂O- SO₂Et tetrahydrofuran-3-yl 1-269 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 1-270 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-2-yl 1-271 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-3-yl 1-272 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-3-yl 1-273 Cl OMe SO₂Me 1-274 Cl OMe SO₂Et 1-275 Cl OEt SO₂Me 1-276 Cl OEt SO₂Et 1-277 Cl OiPr SO₂Me 1-278 Cl OiPr SO₂Et 1-279 Cl O(CH₂)₂OMe SO₂Me 1-280 Cl O(CH₂)₄OMe SO₂Me 1-281 Cl O(CH₂)₄OMe SO₂Et 1-282 Cl O(CH₂)₃OMe SO₂Me 1-283 Cl O(CH₂)₃OMe SO₂Et 1-284 Cl O(CH₂)₂OMe SO₂Me 1-285 Cl O(CH₂)₂OMe SO₂Et 1-286 Cl [1,4]dioxan-2- SO₂Me ylmethoxy 1-287 Cl [1,4]dioxan-2- SO₂Et ylmethoxy 1-288 Cl OCH₂(CO)NMe₂ SO₂Me 1-289 Cl OCH₂(CO)NMe₂ SO₂Et 1-290 Cl SMe SO₂Me 1-291 Cl SOMe SO₂Me 1-292 Br OMe Br 1-293 Br O(CH₂)₂OMe Br 1-294 Br O(CH₂)₂OMe SO₂Me 1-295 Br O(CH₂)₂OMe SO₂Et 1-296 Br O(CH₂)₃OMe SO₂Me 1-297 Br O(CH₂)₃OMe SO₂Et 1-298 Br O(CH₂)₄OMe SO₂Me 1-299 Br O(CH₂)₄OMe SO₂Et 1-300 Br [1,4]dioxan-2- SO₂Me ylmethoxy 1-301 Br [1,4]dioxan-2- SO₂Et ylmethoxy 1-302 I O(CH₂)₂OMe SO₂Me 1-303 I O(CH₂)₂OMe SO₂Et 1-304 I O(CH₂)₃OMe SO₂Me 1-305 I O(CH₂)₃OMe SO₂Et 1-306 I O(CH₂)₄OMe SO₂Me 1-307 I O(CH₂)₄OMe SO₂Et 1-308 I [1,4]dioxan-2- SO₂Me ylmethoxy 1-309 I [1,4]dioxan-2- SO₂Et ylmethoxy 1-310 OMe SMe CF₃ 1-311 OMe SOMe CF₃ 1-312 OMe SO₂Me CF₃ 1-313 OMe SOEt CF₃ 1-314 OMe SO₂Et CF₃ 1-315 OMe S(CH₂)₂OMe CF₃ 1-316 OMe SO(CH₂)₂OMe CF₃ 1-317 OMe SO₂(CH₂)₂OMe CF₃ 1-318 OMe SMe Cl 1-319 OMe SOMe Cl 1-320 OMe SO₂Me Cl 1-321 OMe SEt Cl 1-322 OMe SOEt Cl 1-323 OMe SO2Et Cl 1-324 OMe S(CH₂)₂OMe Cl 1-325 OMe SO(CH₂)₂OMe Cl 1-326 OMe SO₂(CH₂)₂OMe Cl 1-327 OCH₂c-Pr SMe CF₃ 1-328 OCH₂c-Pr SOMe CF₃ 1-329 OCH₂c-Pr SO₂Me CF₃ 1-330 OCH₂c-Pr SEt CF₃ 1-331 OCH₂c-Pr SOEt CF₃ 1-332 OCH₂c-Pr SO₂Et CF₃ 1-333 OCH₂c-Pr S(CH₂)₂OMe CF₃ 1-334 OCH₂c-Pr SO(CH₂)₂OMe CF₃ 1-335 OCH₂c-Pr SO₂(CH₂)₂OMe CF₃ 1-336 OCH₂c-Pr SMe Cl 1-337 OCH₂c-Pr SOMe Cl 1-338 OCH₂c-Pr SO₂Me Cl 1-339 OCH₂c-Pr SEt Cl 1-340 OCH₂c-Pr SOEt Cl 1-341 OCH₂c-Pr SO₂Et Cl 1-342 OCH₂c-Pr S(CH₂)₂OMe Cl 1-343 OCH₂c-Pr SO(CH₂)₂OMe Cl 1-344 OCH₂c-Pr SO₂(CH₂)₂OMe Cl 1-345 OCH₂c-Pr SMe SO₂Me 1-346 OCH₂c-Pr SOMe SO₂Me 1-347 OCH₂c-Pr SO₂Me SO₂Me 1-348 OCH₂c-Pr SEt SO₂Me 1-349 OCH₂c-Pr SOEt SO₂Me 1-350 OCH₂c-Pr SO₂Et SO₂Me 1-351 OCH₂c-Pr S(CH₂)₂OMe SO₂Me 1-352 OCH₂c-Pr SO(CH₂)₂OMe SO₂Me 1-353 OCH₂c-Pr SO₂(CH₂)₂OMe SO₂Me 1-354 SO₂Me F CF₃ 1-355 SO₂Me NH₂ CF₃ 1-356 SO₂Me NHEt Cl 1-357 SMe SEt F 1-358 SMe SMe F 1-359 Cl SMe CF₃ 1-360 Cl S(O)Me CF₃ 1-361 Cl SO₂Me CF₃ 1-362 Cl SO₂Me SO₂Me

TABLE 2 Compounds of the general formula (I) in which A represents CY, V represents hydrogen, W represents fluorine and R represents methyl

Physical data (¹H-NMR, DMSO-d₆, No. X Y Z 400 MHz) 2-1 F H Cl 2-2 F H SO₂Me 2-3 F H SO₂Et 2-4 F H CF₃ 2-5 F H NO₂ 2-6 Cl H Br 2-7 Cl H SMe 2-8 Cl H SOMe 2-9 Cl H SO₂Me 2-10 Cl H SO₂CH₂Cl 2-11 Cl H SEt 2-12 Cl H SO₂Et 2-13 Cl H CF₃ 2-14 Cl H NO₂ 2-15 Cl H pyrazol-1-yl 2-16 Cl H 1H-1,2,4-triazol-1-yl 2-17 Br H Cl 2-18 Br H Br 2-19 Br H SO₂Me 2-20 Br H SO₂Et 2-21 Br H CF₃ 2-22 SO₂Me H Cl 2-23 SO₂Me H Br 2-24 SO₂Me H SMe 2-25 SO₂Me H SOMe 2-26 SO₂Me H SO₂Me 2-27 SO₂Me H SO₂Et 2-28 SO₂Me H CF₃ 2-29 SO₂Et H Cl 2-30 SO₂Et H Br 2-31 SO₂Et H SMe 2-32 SO₂Et H SOMe 2-33 SO₂Et H SO₂Me 2-34 SO₂Et H CF₃ 2-35 NO₂ H F 2-36 NO₂ H Cl 2-37 NO₂ H Br 2-38 NO₂ H I 2-39 NO₂ H CN 2-40 NO₂ H SO₂Me 2-41 NO₂ H SO₂Et 2-42 NO₂ H CF₃ 2-43 Me H Cl 2-44 Me H Br 2-45 Me H SMe 2-46 Me H SO₂Me 2-47 Me H SO₂CH₂Cl 2-48 Me H SEt 2-49 Me H SO₂Et 2-50 Me H CF₃ 2-51 CH₂SO₂Me H CF₃ 2-52 Et H Cl 2-53 Et H Br 2-54 Et H SMe 2-55 Et H SO₂Me 2-56 Et H SO₂CH₂Cl 2-57 Et H SEt 2-58 Et H SO₂Et 2-59 Et H CF₃ 2-60 CF₃ H Cl 2-61 CF₃ H Br 2-62 CF₃ H SO₂Me 2-63 CF₃ H SO₂Et 2-64 CF₃ H CF₃ 2-65 NO₂ NH₂ F 2-66 NO₂ NHMe F 2-67 NO₂ NMe₂ F 2-68 NO₂ Me Cl 2-69 NO₂ NH₂ Cl 2-70 NO₂ NHMe Cl 2-71 NO₂ NMe₂ Cl 2-72 NO₂ NH₂ Br 2-73 NO₂ NHMe Br 2-74 NO₂ NMe₂ Br 2-75 NO₂ NH₂ CF₃ 2-76 NO₂ NMe₂ CF₃ 2-77 NO₂ NH₂ SO₂Me 2-78 NO₂ NH₂ SO₂Et 2-79 NO₂ NHMe SO₂Me 2-80 NO₂ NMe₂ SO₂Me 2-81 NO₂ NMe₂ SO₂Et 2-82 NO₂ NH₂ 1H-1,2,4-triazol-1-yl 2-83 NO₂ NHMe 1H-1,2,4-triazol-1-yl 2-84 NO₂ NMe₂ 1H-1,2,4-triazol-1-yl 2-85 Me SMe H 2-86 Me SOMe H 2-87 Me SO₂Me H 2-88 Me SEt H 2-89 Me SOEt H 2-90 Me SO₂Et H 2-91 Me S(CH₂)₂OMe H 2-92 Me SO(CH₂)₂OMe H 2-93 Me SO₂(CH₂)₂OMe H 2-94 Me F F 2-95 Me F Cl 2-96 Me SEt F 2-97 Me SOEt F 2-98 Me SO₂Et F 2-99 Me Me Cl 2-100 Me F Cl 2-101 Me Cl Cl 2-102 Me NH₂ Cl 2-103 Me NHMe Cl 2-104 Me NMe₂ Cl 2-105 Me O(CH₂)₂OMe Cl 2-106 Me O(CH₂)₃OMe Cl 2-107 Me O(CH₂)₄OMe Cl 2-108 Me OCH₂CONMe₂ Cl 2-109 Me O(CH₂)₂—CO—NMe₂ Cl 2-110 Me O(CH₂)₂—NH(CO)NMe₂ Cl 2-111 Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 2-112 Me O(CH₂)₂—NHCO₂Me Cl 2-113 Me O—CH₂—NHSO₂cPr Cl 2-114 Me O(CH₂)-5-2,4- Cl dimethyl-2,4- dihydro-3H- 1,2,4-triazol-3- one 2-115 Me O(CH₂)-3,5- Cl dimethyl-1,2- oxazol-4-yl 2-116 Me SMe Cl 2-117 Me SOMe Cl 2-118 Me SO₂Me Cl 2-119 Me SEt Cl 2-120 Me SOEt Cl 2-121 Me SO₂Et Cl 2-122 Me S(CH₂)₂OMe Cl 2-123 Me SO(CH₂)₂OMe Cl 2-124 Me SO₂(CH₂)₂OMe Cl 2-125 2-126 Me NHMe Br 2-127 Me NMe₂ Br 2-128 Me O(CH₂)CONEt₂ Br 2-129 Me O(CH₂)-5- Br pyrrolidin-2-one 2-130 Me SMe Br 2-131 Me SOMe Br 2-132 Me SO₂Me Br 2-133 Me SEt Br 2-134 Me SOEt Br 2-135 Me SO₂Et Br 2-136 Me SMe I 2-137 Me SOMe I 2-138 Me SO₂Me I 2-139 Me SEt I 2-140 Me SOEt I 2-141 Me SO₂Et I 2-142 Me Cl CF₃ 2-143 Me SMe CF₃ 2-144 Me SOMe CF₃ 2-145 Me SO₂Me CF₃ 2-146 Me SEt CF₃ 2-147 Me SOEt CF₃ 2-148 Me SO₂Et CF₃ 2-149 Me S(CH₂)₂OMe CF₃ 2-150 Me SO(CH₂)₂OMe CF₃ 2-151 Me SO₂(CH₂)₂OMe CF₃ 2-152 Me Me SO₂Me 2-153 Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 2-154 Me 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 2-155 Me 5-cyanomethyl- SO₂Me 4,5-dihydro-1,2- oxazol-3-yl 2-156 Me 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 2-157 Me NH₂ SO₂Me 2-158 Me NHMe SO₂Me 2-159 Me NMe₂ SO₂Me 2-160 Me NH(CH₂)₂OMe SO₂Me 2-161 Me pyrazol-1-yl SO₂Me 2-162 Me OH SO₂Me 2-163 Me OMe SO₂Me 2-164 Me OMe SO₂Et 2-165 Me OEt SO₂Me 2-166 Me OEt SO₂Et 2-167 Me OiPr SO₂Me 2-168 Me OiPr SO₂Et 2-169 Me O(CH₂)₂OMe SO₂Me 2-170 Me O(CH₂)₂OMe SO₂Et 2-171 Me O(CH₂)₃OMe SO₂Me 2-172 Me O(CH₂)₃OMe SO₂Et 2-173 Me O(CH₂)₄OMe SO₂Me 2-174 Me O(CH₂)₄OMe SO₂Et 2-175 Me O(CH₂)₂NHSO2Me SO₂Me 2-176 Me O(CH₂)₂NHSO2Me SO₂Et 2-177 Me OCH₂(CO)NMe₂ SO₂Me 2-178 Me OCH₂(CO)NMe₂ SO₂Et 2-179 Me [1,4]dioxan-2- SO₂Me ylmethoxy 2-180 Me [1,4]dioxan-2- SO₂Et ylmethoxy 2-181 Me O(CH₂)₂—O-(3,5- SO₂Me di- methoxypyrimidin- 2-yl) 2-182 Me Cl SO₂Me 2-183 Me SMe SO₂Me 2-184 Me SOMe SO₂Me 2-185 Me SO₂Me SO₂Me 2-186 Me SO₂Me SO₂Et 2-187 Me SEt SO₂Me 2-188 Me SOEt SO₂Me 2-189 Me SO₂Et SO₂Me 2-190 Me S(CH₂)₂OMe SO₂Me 2-191 Me SO(CH₂)₂OMe SO₂Me 2-192 Me SO₂(CH₂)₂OMe SO₂Me 2-193 CH₂SMe OMe SO₂Me 2-194 CH₂OMe OMe SO₂Me 2-195 CH₂O(CH₂)₂ NH(CH₂)₂OEt SO₂Me OMe 2-196 CH₂O(CH₂)₂ NH(CH₂)₃OEt SO₂Me OMe 2-197 CH₂O(CH₂)₃ OMe SO₂Me OMe 2-198 CH₂O(CH₂)₂ NH(CH₂)₂OMe SO₂Me OMe 2-199 CH₂O(CH₂)₂ NH(CH₂)₃OMe SO₂Me OMe 2-200 Et SMe Cl 2-201 Et SO₂Me Cl 2-202 Et SMe CF₃ 2-203 Et SO₂Me CF₃ 2-204 Et F SO₂Me 2-205 Et NH(CH₂)₂OMe SO₂Me 2-206 iPr SO₂Me CF₃ 2-207 cPr SO₂Me CF₃ 2-208 CF₃ O(CH₂)₂OMe F 2-209 CF₃ O(CH₂)₃OMe F 2-210 CF₃ OCH₂CONMe₂ F 2-211 CF₃ [1,4]dioxan-2- F ylmethoxy 2-212 CF₃ O(CH₂)₂OMe Cl 2-213 CF₃ O(CH₂)₃OMe Cl 2-214 CF₃ OCH₂CONMe₂ Cl 2-215 CF₃ [1,4]dioxan-2- Cl ylmethoxy 2-216 CF₃ O(CH₂)₂OMe Br 2-217 CF₃ O(CH₂)₃OMe Br 2-218 CF₃ OCH₂CONMe₂ Br 2-219 CF₃ [1,4]dioxan-2- Br ylmethoxy 2-220 CF₃ O(CH₂)₂OMe I 2-221 CF₃ O(CH₂)₃OMe I 2-222 CF₃ OCH₂CONMe₂ I 2-223 CF₃ [1,4]dioxan-2- I ylmethoxy 2-224 CF₃ F SO₂Me 2-225 CF₃ F SO₂Et 2-226 CF₃ O(CH₂)₂OMe SO₂Me 2-227 CF₃ O(CH₂)₂OMe SO₂Et 2-228 CF₃ O(CH₂)₃OMe SO₂Me 2-229 CF₃ O(CH₂)₃OMe SO₂Et 2-230 CF₃ OCH₂CONMe₂ SO₂Me 2-231 CF₃ OCH₂CONMe₂ SO₂Et 2-232 CF₃ [1,4]dioxan-2- SO₂Me ylmethoxy 2-233 CF₃ [1,4]dioxan-2- SO₂Et ylmethoxy 2-234 F SMe CF₃ 2-235 F SOMe CF₃ 2-236 Cl Me Cl 2-237 Cl OCH₂CHCH₂ Cl 2-238 Cl OCH₂CHF₂ Cl 2-239 Cl O(CH₂)₂OMe Cl 2-240 Cl OCH₂(CO)NMe₂ Cl 2-241 Cl O(CH₂)-5- Cl pyrrolidin-2-one 2-242 Cl SMe Cl 12.59 ppm (bs, 1H), 7.86 ppm (d, 1H); 2.41 ppm (s, 3H). 2-243 Cl SOMe Cl 11.60 ppm (bs, 1H), 7.24 ppm (d, 1H); 3.07 ppm (s, 3H). 2-244 Cl SO₂Me Cl 2-245 Cl F SMe 2-246 Cl Cl SO₂Me 2-247 Cl COOMe SO₂Me 2-248 Cl CONMe₂ SO₂Me 2-249 Cl CONMe(OMe) SO₂Me 2-250 Cl CH₂OMe SO₂Me 2-251 Cl CH₂OMe SO₂Et 2-252 Cl CH₂OEt SO₂Me 2-253 Cl CH₂OEt SO₂Et 2-254 Cl CH₂OCH₂CHF₂ SO₂Me 2-255 Cl CH₂OCH₂CF₃ SO₂Me 2-256 Cl CH₂OCH₂CF₃ SO₂Et 2-257 Cl CH₂OCH₂CF₂CHF₂ SO₂Me 2-258 Cl CH₂O-c-pentyl SO₂Me 2-259 Cl CH₂PO(OMe)₂ SO₂Me 2-260 Cl 4,5-dihydro-1,2- SMe oxazol-3-yl 2-261 Cl 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 2-262 Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 2-263 Cl 5-cyanomethyl- SO₂Me 4,5-dihydro-1,2- oxazol-3-yl 2-264 Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 2-265 Cl 5- SO₂Et (methoxymethyl)- 4,5-dihydro-1,2- oxazol-3-yl 2-266 Cl 5- SO₂Et (methoxymethyl)- 5-methyl-4,5- dihydro-1,2- oxazol-3-yl 2-267 Cl CH₂O- SO₂Me tetrahydrofuran- 3-yl 2-268 Cl CH₂O- SO₂Et tetrahydrofuran- 3-yl 2-269 Cl CH₂OCH₂- SO₂Me tetrahydrofuran- 2-yl 2-270 Cl CH₂OCH₂- SO₂Et tetrahydrofuran- 2-yl 2-271 Cl CH₂OCH₂- SO₂Me tetrahydrofuran- 3-yl 2-272 Cl CH₂OCH₂- SO₂Et tetrahydrofuran- 3-yl 2-273 Cl OMe SO₂Me 2-274 Cl OMe SO₂Et 2-275 Cl OEt SO₂Me 2-276 Cl OEt SO₂Et 2-277 Cl OiPr SO₂Me 2-278 Cl OiPr SO₂Et 2-279 Cl O(CH₂)₂OMe SO₂Me 2-280 Cl O(CH₂)₄OMe SO₂Me 2-281 Cl O(CH₂)₄OMe SO₂Et 2-282 Cl O(CH₂)₃OMe SO₂Me 2-283 Cl O(CH₂)₃OMe SO₂Et 2-284 Cl O(CH₂)₂OMe SO₂Me 2-285 Cl O(CH₂)₂OMe SO₂Et 2-286 Cl [1,4]dioxan-2- SO₂Me ylmethoxy 2-287 Cl [1,4]dioxan-2- SO₂Et ylmethoxy 2-288 Cl OCH₂(CO)NMe₂ SO₂Me 2-289 Cl OCH₂(CO)NMe₂ SO₂Et 2-290 Cl SMe SO₂Me 2-291 Cl SOMe SO₂Me 2-292 Br OMe Br 2-293 Br O(CH₂)₂OMe Br 2-294 Br O(CH₂)₂OMe SO₂Me 2-295 Br O(CH₂)₂OMe SO₂Et 2-296 Br O(CH₂)₃OMe SO₂Me 2-297 Br O(CH₂)₃OMe SO₂Et 2-298 Br O(CH₂)₄OMe SO₂Me 2-299 Br O(CH₂)₄OMe SO₂Et 2-300 Br [1,4]dioxan-2- SO₂Me ylmethoxy 2-301 Br [1,4]dioxan-2- SO₂Et ylmethoxy 2-302 I O(CH₂)₂OMe SO₂Me 2-303 I O(CH₂)₂OMe SO₂Et 2-304 I O(CH₂)₃OMe SO₂Me 2-305 I O(CH₂)₃OMe SO₂Et 2-306 I O(CH₂)₄OMe SO₂Me 2-307 I O(CH₂)₄OMe SO₂Et 2-308 I [1,4]dioxan-2- SO₂Me ylmethoxy 2-309 I [1,4]dioxan-2- SO₂Et ylmethoxy 2-310 OMe SMe CF₃ 2-311 OMe SOMe CF₃ 2-312 OMe SO₂Me CF₃ 2-313 OMe SOEt CF₃ 2-314 OMe SO₂Et CF₃ 2-315 OMe S(CH₂)₂OMe CF₃ 2-316 OMe SO(CH₂)₂OMe CF₃ 2-317 OMe SO₂(CH₂)₂OMe CF₃ 2-318 OMe SMe Cl 2-319 OMe SOMe Cl 2-320 OMe SO₂Me Cl 2-321 OMe SEt Cl 2-322 OMe SOEt Cl 2-323 OMe SO2Et Cl 2-324 OMe S(CH₂)₂OMe Cl 2-325 OMe SO(CH₂)₂OMe Cl 2-326 OMe SO₂(CH₂)₂OMe Cl 2-327 OCH₂c-Pr SMe CF₃ 2-328 OCH₂c-Pr SOMe CF₃ 2-329 OCH₂c-Pr SO₂Me CF₃ 2-330 OCH₂c-Pr SEt CF₃ 2-331 OCH₂c-Pr SOEt CF₃ 2-332 OCH₂c-Pr SO₂Et CF₃ 2-333 OCH₂c-Pr S(CH₂)₂OMe CF₃ 2-334 OCH₂c-Pr SO(CH₂)₂OMe CF₃ 2-335 OCH₂c-Pr SO₂(CH₂)₂OMe CF₃ 2-336 OCH₂c-Pr SMe Cl 2-337 OCH₂c-Pr SOMe Cl 2-338 OCH₂c-Pr SO₂Me Cl 2-339 OCH₂c-Pr SEt Cl 2-340 OCH₂c-Pr SOEt Cl 2-341 OCH₂c-Pr SO₂Et Cl 2-342 OCH₂c-Pr S(CH₂)₂OMe Cl 2-343 OCH₂c-Pr SO(CH₂)₂OMe Cl 2-344 OCH₂c-Pr SO₂(CH₂)₂OMe Cl 2-345 OCH₂c-Pr SMe SO₂Me 2-346 OCH₂c-Pr SOMe SO₂Me 2-347 OCH₂c-Pr SO₂Me SO₂Me 2-348 OCH₂c-Pr SEt SO₂Me 2-349 OCH₂c-Pr SOEt SO₂Me 2-350 OCH₂c-Pr SO₂Et SO₂Me 2-351 OCH₂c-Pr S(CH₂)₂OMe SO₂Me 2-352 OCH₂c-Pr SO(CH₂)₂OMe SO₂Me 2-353 OCH₂c-Pr SO₂(CH₂)₂OMe SO₂Me 2-354 SO₂Me F CF₃ 2-355 SO₂Me NH₂ CF₃ 2-356 SO₂Me NHEt Cl 2-357 SMe SEt F 2-358 SMe SMe F 2-359 Cl SMe CF₃ 2-360 Cl S(O)Me CF₃ 2-361 Cl SO₂Me CF₃ 2-362 Cl SO₂Me SO₂Me

TABLE 3 Compounds of the general formula (I) in which A represents CY, V represents hydrogen, W represents fluorine and R represents ethyl

Physical data (¹H-NMR, DMSO-d₆, No. X Y Z 400 MHz) 3-1 F H Cl 3-2 F H SO₂Me 3-3 F H SO₂Et 3-4 F H CF₃ 3-5 F H NO₂ 3-6 Cl H Br 3-7 Cl H SMe 3-8 Cl H SOMe 3-9 Cl H SO₂Me 3-10 Cl H SO₂CH₂Cl 3-11 Cl H SEt 3-12 Cl H SO₂Et 3-13 Cl H CF₃ 3-14 Cl H NO₂ 3-15 Cl H pyrazol- 1-yl 3-16 Cl H 1H-1,2,4- triazol- 1-yl 3-17 Br H Cl 3-18 Br H Br 3-19 Br H SO₂Me 3-20 Br H SO₂Et 3-21 Br H CF₃ 3-22 SO₂Me H Cl 3-23 SO₂Me H Br 3-24 SO₂Me H SMe 3-25 SO₂Me H SOMe 3-26 SO₂Me H SO₂Me 3-27 SO₂Me H SO₂Et 3-28 SO₂Me H CF₃ 3-29 SO₂Et H Cl 3-30 SO₂Et H Br 3-31 SO₂Et H SMe 3-32 SO₂Et H SOMe 3-33 SO₂Et H SO₂Me 3-34 SO₂Et H CF₃ 3-35 NO₂ H F 3-36 NO₂ H Cl 3-37 NO₂ H Br 3-38 NO₂ H I 3-39 NO₂ H CN 3-40 NO₂ H SO₂Me 3-41 NO₂ H SO₂Et 3-42 NO₂ H CF₃ 3-43 Me H Cl 3-44 Me H Br 3-45 Me H SMe 3-46 Me H SO₂Me 3-47 Me H SO₂CH₂Cl 3-48 Me H SEt 3-49 Me H SO₂Et 3-50 Me H CF₃ 3-51 CH₂SO₂Me H CF₃ 3-52 Et H Cl 3-53 Et H Br 3-54 Et H SMe 3-55 Et H SO₂Me 3-56 Et H SO₂CH₂Cl 3-57 Et H SEt 3-58 Et H SO₂Et 3-59 Et H CF₃ 3-60 CF₃ H Cl 3-61 CF₃ H Br 3-62 CF₃ H SO₂Me 3-63 CF₃ H SO₂Et 3-64 CF₃ H CF₃ 3-65 NO₂ NH₂ F 3-66 NO₂ NHMe F 3-67 NO₂ NMe₂ F 3-68 NO₂ Me Cl 3-69 NO₂ NH₂ Cl 3-70 NO₂ NHMe Cl 3-71 NO₂ NMe₂ Cl 3-72 NO₂ NH₂ Br 3-73 NO₂ NHMe Br 3-74 NO₂ NMe₂ Br 3-75 NO₂ NH₂ CF₃ 3-76 NO₂ NMe₂ CF₃ 3-77 NO₂ NH₂ SO₂Me 3-78 NO₂ NH₂ SO₂Et 3-79 NO₂ NHMe SO₂Me 3-80 NO₂ NMe₂ SO₂Me 3-81 NO₂ NMe₂ SO₂Et 3-82 NO₂ NH₂ 1H-1,2,4- triazol- 1-yl 3-83 NO₂ NHMe 1H-1,2,4- triazol- 1-yl 3-84 NO₂ NMe₂ 1H-1,2,4- triazol- 1-yl 3-85 Me SMe H 3-86 Me SOMe H 3-87 Me SO₂Me H 3-88 Me SEt H 3-89 Me SOEt H 3-90 Me SO₂Et H 3-91 Me S(CH₂)₂OMe H 3-92 Me SO(CH₂)₂OMe H 3-93 Me SO₂(CH₂)₂OMe H 3-94 Me F F 3-95 Me F Cl 3-96 Me SEt F 3-97 Me SOEt F 3-98 Me SO₂Et F 3-99 Me Me Cl 3-100 Me F Cl 3-101 Me Cl Cl 3-102 Me NH₂ Cl 3-103 Me NHMe Cl 3-104 Me NMe₂ Cl 3-105 Me O(CH₂)₂OMe Cl 3-106 Me O(CH₂)₃OMe Cl 3-107 Me O(CH₂)₄OMe Cl 3-108 Me OCH₂CONMe₂ Cl 3-109 Me O(CH₂)₂—CONMe₂ Cl 3-110 Me O(CH₂)₂—NH(CO)NMe₂ Cl 3-111 Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 3-112 Me O(CH₂)₂NHCO₂Me Cl 3-113 Me OCH₂NHSO₂cPr Cl 3-114 Me O(CH₂)-5-2,4-di- Cl methyl-2,4-dihydro- 3H-1,2,4-triazol-3- one 3-115 Me O(CH₂)-3,5- Cl dimethyl-1,2- oxazol-4-yl 3-116 Me SMe Cl 3-117 Me SOMe Cl 3-118 Me SO₂Me Cl 3-119 Me SEt Cl 3-120 Me SOEt Cl 3-121 Me SO₂Et Cl 3-122 Me S(CH₂)₂OMe Cl 3-123 Me SO(CH₂)₂OMe Cl 3-124 Me SO₂(CH₂)₂OMe Cl 3-125 Me NH₂ Br 3-126 Me NHMe Br 3-127 Me NMe₂ Br 3-128 Me OCH₂CONMe₂ Br 3-129 Me O(CH₂)-5- Br pyrrolidin-2-one 3-130 Me SMe Br 3-131 Me SOMe Br 3-132 Me SO₂Me Br 3-133 Me SEt Br 3-134 Me SOEt Br 3-135 Me SO₂Et Br 3-136 Me SMe I 3-137 Me SOMe I 3-138 Me SO₂Me I 3-139 Me SEt I 3-140 Me SOEt I 3-141 Me SO₂Et I 3-142 Me Cl CF₃ 3-143 Me SMe CF₃ 3-144 Me SOMe CF₃ 3-145 Me SO₂Me CF₃ 3-146 Me SEt CF₃ 3-147 Me SOEt CF₃ 3-148 Me SO₂Et CF₃ 3-149 Me S(CH₂)₂OMe CF₃ 3-150 Me SO(CH₂)₂OMe CF₃ 3-151 Me SO₂(CH₂)₂OMe CF₃ 3-152 Me Me SO₂Me 3-153 Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 3-154 Me 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 3-155 Me 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol- 3-yl 3-156 Me 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 3-157 Me NH₂ SO₂Me 3-158 Me NHMe SO₂Me 3-159 Me NMe₂ SO₂Me 3-160 Me NH(CH₂)₂OMe SO₂Me 3-161 Me Pyrazol-1-yl SO₂Me 3-162 Me OH SO₂Me 3-163 Me OMe SO₂Me 3-164 Me OMe SO₂Et 3-165 Me OEt SO₂Me 3-166 Me OEt SO₂Et 3-167 Me OiPr SO₂Me 3-168 Me OiPr SO₂Et 3-169 Me O(CH₂)₂OMe SO₂Me 3-170 Me O(CH₂)₂OMe SO₂Et 3-171 Me O(CH₂)₃OMe SO₂Me 3-172 Me O(CH₂)₃OMe SO₂Et 3-173 Me O(CH₂)₄OMe SO₂Me 3-174 Me O(CH₂)₄OMe SO₂Et 3-175 Me O(CH₂)₂NHSO2Me SO₂Me 3-176 Me O(CH₂)₂NHSO2Me SO₂Et 3-177 Me OCH₂(CO)NMe₂ SO₂Me 3-178 Me OCH₂(CO)NMe₂ SO₂Et 3-179 Me [1,4]dioxan-2- SO₂Me ylmethoxy 3-180 Me [1,4]dioxan-2- SO₂Et ylmethoxy 3-181 Me O(CH₂)₂—O-(3,5- SO₂Me dimethoxypyrimidin- 2-yl) 3-182 Me Cl SO₂Me 3-183 Me SMe SO₂Me 3-184 Me SOMe SO₂Me 3-185 Me SO₂Me SO₂Me 3-186 Me SO₂Me SO₂Et 3-187 Me SEt SO₂Me 3-188 Me SOEt SO₂Me 3-189 Me SO₂Et SO₂Me 3-190 Me S(CH₂)₂OMe SO₂Me 3-191 Me SO(CH₂)₂OMe SO₂Me 3-192 Me SO₂(CH₂)₂OMe SO2Me 3-193 CH₂SMe OMe SO₂Me 3-194 CH₂OMe OMe SO₂Me 3-195 CH₂O(CH₂)₂ NH(CH₂)₂OEt SO₂Me OMe 3-196 CH₂O(CH₂)₂ NH(CH₂)₃OEt SO₂Me OMe 3-197 CH₂O(CH₂)₃ OMe SO₂Me OMe 3-198 CH₂O(CH₂)₂ NH(CH₂)₂OMe SO₂Me OMe 3-199 CH₂O(CH₂)₂ NH(CH₂)₃OMe SO₂Me OMe 3-200 Et SMe Cl 3-201 Et SO₂Me Cl 3-202 Et SMe CF₃ 3-203 Et SO₂Me CF₃ 3-204 Et F SO₂Me 3-205 Et NH(CH₂)₂OMe SO₂Me 3-206 iPr SO₂Me CF₃ 3-207 cPr SO₂Me CF₃ 3-208 CF₃ O(CH₂)₂OMe F 3-209 CF₃ O(CH₂)₃OMe F 3-210 CF₃ OCH₂CONMe₂ F 3-211 CF₃ [1,4]dioxan-2- F ylmethoxy 3-212 CF₃ O(CH₂)₂OMe Cl 3-213 CF₃ O(CH₂)₃OMe Cl 3-214 CF₃ OCH₂CONMe₂ Cl 3-215 CF₃ [1,4]dioxan-2- Cl ylmethoxy 3-216 CF₃ O(CH₂)₂OMe Br 3-217 CF₃ O(CH₂)₃OMe Br 3-218 CF₃ OCH₂CONMe₂ Br 3-219 CF₃ [1,4]dioxan-2- Br ylmethoxy 3-220 CF₃ O(CH₂)₂OMe I 3-221 CF₃ O(CH₂)₃OMe I 3-222 CF₃ OCH₂CONMe₂ I 3-223 CF₃ [1,4]dioxan-2- I ylmethoxy 3-224 CF₃ F SO₂Me 3-225 CF₃ F SO₂Et 3-226 CF₃ O(CH₂)₂OMe SO₂Me 3-227 CF₃ O(CH₂)₂OMe SO₂Et 3-228 CF₃ O(CH₂)₃OMe SO₂Me 3-229 CF₃ O(CH₂)₃OMe SO₂Et 3-230 CF₃ OCH₂CONMe₂ SO₂Me 3-231 CF₃ OCH₂CONMe₂ SO₂Et 3-232 CF₃ [1,4]dioxan-2- SO₂Me ylmethoxy 3-233 CF₃ [1,4]dioxan-2- SO₂Et ylmethoxy 3-234 F SMe CF₃ 3-235 F SOMe CF₃ 3-236 Cl Me Cl 3-237 Cl OCH₂CHCH₂ Cl 3-238 Cl OCH₂CHF₂ Cl 3-239 Cl O(CH₂)₂OMe Cl 3-240 Cl OCH₂(CO)NMe₂ Cl 3-241 Cl O(CH₂)-5- Cl pyrrolidin-2-one 3-242 Cl SMe Cl 3-243 Cl SOMe Cl 3-244 Cl SO₂Me Cl 3-245 Cl F SMe 3-246 Cl Cl SO₂Me 3-247 Cl COOMe SO₂Me 3-248 Cl CONMe₂ SO₂Me 3-249 Cl CONMe(OMe) SO₂Me 3-250 Cl CH₂OMe SO₂Me 3-251 Cl CH₂OMe SO₂Et 3-252 Cl CH₂OEt SO₂Me 3-253 Cl CH₂OEt SO₂Et 3-254 Cl CH₂OCH₂CHF₂ SO₂Me 3-255 Cl CH₂OCH₂CF₃ SO₂Me 3-256 Cl CH₂OCH₂CF₃ SO₂Et 3-257 Cl CH₂OCH₂CF₂CHF₂ SO₂Me 3-258 Cl CH₂O-c-pentyl SO₂Me 3-259 Cl CH₂PO(OMe)₂ SO₂Me 3-260 Cl 4,5-dihydro-1,2- SMe oxazol-3-yl 3-261 Cl 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 3-262 Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 3-263 Cl 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol- 3-yl 3-264 Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 3-265 Cl 5-(methoxymethyl)- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 3-266 Cl 5-(methoxymethyl)- SO₂Et 5-methyl-4,5- dihydro-1,2-oxazol-3-yl 3-267 Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 3-268 Cl CH₂O- SO₂Et tetrahydrofuran-3-yl 3-269 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 3-270 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-2-yl 3-271 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-3-yl 3-272 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-3-yl 3-273 Cl OMe SO₂Me 3-274 Cl OMe SO₂Et 3-275 Cl OEt SO₂Me 3-276 Cl OEt SO₂Et 3-277 Cl OiPr SO₂Me 3-278 Cl OiPr SO₂Et 3-279 Cl O(CH₂)₂OMe SO₂Me 3-280 Cl O(CH₂)₄OMe SO₂Me 3-281 Cl O(CH₂)₄OMe SO₂Et 3-282 Cl O(CH₂)₃OMe SO₂Me 3-283 Cl O(CH₂)₃OMe SO₂Et 3-284 Cl O(CH₂)₂OMe SO₂Me 3-285 Cl O(CH₂)₂OMe SO₂Et 3-286 Cl [1,4]dioxan-2- SO₂Me ylmethoxy 3-287 Cl [1,4]dioxan-2- SO₂Et ylmethoxy 3-288 Cl OCH₂(CO)NMe₂ SO₂Me 3-289 Cl OCH₂(CO)NMe₂ SO₂Et 3-290 Cl SMe SO₂Me 3-291 Cl SOMe SO₂Me 3-292 Br OMe Br 3-293 Br O(CH₂)₂OMe Br 3-294 Br O(CH₂)₂OMe SO₂Me 3-295 Br O(CH₂)₂OMe SO₂Et 3-296 Br O(CH₂)₃OMe SO₂Me 3-297 Br O(CH₂)₃OMe SO₂Et 3-298 Br O(CH₂)₄OMe SO₂Me 3-299 Br O(CH₂)₄OMe SO₂Et 3-300 Br [1,4]dioxan-2- SO₂Me ylmethoxy 3-301 Br [1,4]dioxan-2- SO₂Et ylmethoxy 3-302 I O(CH₂)₂OMe SO₂Me 3-303 I O(CH₂)₂OMe SO₂Et 3-304 I O(CH₂)₃OMe SO₂Me 3-305 I O(CH₂)₃OMe SO₂Et 3-306 I O(CH₂)₄OMe SO₂Me 3-307 I O(CH₂)₄OMe SO₂Et 3-308 I [1,4]dioxan-2- SO₂Me ylmethoxy 3-309 I [1,4]dioxan-2- SO₂Et ylmethoxy 3-310 OMe SMe CF₃ 3-311 OMe SOMe CF₃ 3-312 OMe SO₂Me CF₃ 3-313 OMe SOEt CF₃ 3-314 OMe SO₂Et CF₃ 3-315 OMe S(CH₂)₂OMe CF₃ 3-316 OMe SO(CH₂)₂OMe CF₃ 3-317 OMe SO₂(CH₂)₂OMe CF₃ 3-318 OMe SMe Cl 3-319 OMe SOMe Cl 3-320 OMe SO₂Me Cl 3-321 OMe SEt Cl 3-322 OMe SOEt Cl 3-323 OMe SO2Et Cl 3-324 OMe S(CH₂)₂OMe Cl 3-325 OMe SO(CH₂)₂OMe Cl 3-326 OMe SO₂(CH₂)₂OMe Cl 3-327 OCH₂c-Pr SMe CF₃ 3-328 OCH₂c-Pr SOMe CF₃ 3-329 OCH₂c-Pr SO₂Me CF₃ 3-330 OCH₂c-Pr SEt CF₃ 3-331 OCH₂c-Pr SOEt CF₃ 3-332 OCH₂c-Pr SO₂Et CF₃ 3-333 OCH₂c-Pr S(CH₂)₂OMe CF₃ 3-334 OCH₂c-Pr SO(CH₂)₂OMe CF₃ 3-335 OCH₂c-Pr SO₂(CH₂)₂OMe CF₃ 3-336 OCH₂c-Pr SMe Cl 3-337 OCH₂c-Pr SOMe Cl 3-338 OCH₂c-Pr SO₂Me Cl 3-339 OCH₂c-Pr SEt Cl 3-340 OCH₂c-Pr SOEt Cl 3-341 OCH₂c-Pr SO₂Et Cl 3-342 OCH₂c-Pr S(CH₂)₂OMe Cl 3-343 OCH₂c-Pr SO(CH₂)₂OMe Cl 3-344 OCH₂c-Pr SO₂(CH₂)₂OMe Cl 3-345 OCH₂c-Pr SMe SO₂Me 3-346 OCH₂c-Pr SOMe SO₂Me 3-347 OCH₂c-Pr SO₂Me SO₂Me 3-348 OCH₂c-Pr SEt SO₂Me 3-349 OCH₂c-Pr SOEt SO₂Me 3-350 OCH₂c-Pr SO₂Et SO₂Me 3-351 OCH₂c-Pr S(CH₂)₂OMe SO₂Me 3-352 OCH₂c-Pr SO(CH₂)₂OMe SO₂Me 3-353 OCH₂c-Pr SO₂(CH₂)₂OMe SO₂Me 3-354 SO₂Me F CF₃ 3-355 SO₂Me NH₂ CF₃ 3-356 SO₂Me NHEt Cl 3-357 SMe SEt F 3-358 SMe SMe F 3-359 Cl SMe CF₃ 3-360 Cl S(O)Me CF₃ 3-361 Cl SO₂Me CF₃ 3-362 Cl SO₂Me SO₂Me

TABLE 4 Compounds of the general formula (I) in which A represents CY, V represents hydrogen, W represents fluorine and R represents trifluoromethyl

Physical data (¹H-NMR, DMSO-d₆, No. X Y Z 400 MHz) 4-1 F H Cl 4-2 F H SO₂Me 4-3 F H SO₂Et 4-4 F H CF₃ 4-5 F H NO₂ 4-6 Cl H Br 4-7 Cl H SMe 4-8 Cl H SOMe 4-9 Cl H SO₂Me 4-10 Cl H SO₂CH₂Cl 4-11 Cl H SEt 4-12 Cl H SO₂Et 4-13 Cl H CF₃ 4-14 Cl H NO₂ 4-15 Cl H pyrazol-1-yl 4-16 Cl H 1H-1,2,4-triazol- 1-yl 4-17 Br H Cl 4-18 Br H Br 4-19 Br H SO₂Me 4-20 Br H SO₂Et 4-21 Br H CF₃ 4-22 SO₂Me H Cl 4-23 SO₂Me H Br 4-24 SO₂Me H SMe 4-25 SO₂Me H SOMe 4-26 SO₂Me H SO₂Me 4-27 SO₂Me H SO₂Et 4-28 SO₂Me H CF₃ 4-29 SO₂Et H Cl 4-30 SO₂Et H Br 4-31 SO₂Et H SMe 4-32 SO₂Et H SOMe 4-33 SO₂Et H SO₂Me 4-34 SO₂Et H CF₃ 4-35 NO₂ H F 4-36 NO₂ H Cl 4-37 NO₂ H Br 4-38 NO₂ H I 4-39 NO₂ H CN 4-40 NO₂ H SO₂Me 4-41 NO₂ H SO₂Et 4-42 NO₂ H CF₃ 4-43 Me H Cl 4-44 Me H Br 4-45 Me H SMe 4-46 Me H SO₂Me 4-47 Me H SO₂CH₂Cl 4-48 Me H SEt 4-49 Me H SO₂Et 4-50 Me H CF₃ 4-51 CH₂SO₂Me H CF₃ 4-52 Et H Cl 4-53 Et H Br 4-54 Et H SMe 4-55 Et H SO₂Me 4-56 Et H SO₂CH₂Cl 4-57 Et H SEt 4-58 Et H SO₂Et 4-59 Et H CF₃ 4-60 CF₃ H Cl 4-61 CF₃ H Br 4-62 CF₃ H SO₂Me 4-63 CF₃ H SO₂Et 4-64 CF₃ H CF₃ 4-65 NO₂ NH₂ F 4-66 NO₂ NHMe F 4-67 NO₂ NMe₂ F 4-68 NO₂ Me Cl 4-69 NO₂ NH₂ Cl 4-70 NO₂ NHMe Cl 4-71 NO₂ NMe₂ Cl 4-72 NO₂ NH₂ Br 4-73 NO₂ NHMe Br 4-74 NO₂ NMe₂ Br 4-75 NO₂ NH₂ CF₃ 4-76 NO₂ NMe₂ CF₃ 4-77 NO₂ NH₂ SO₂Me 4-78 NO₂ NH₂ SO₂Et 4-79 NO₂ NHMe SO₂Me 4-80 NO₂ NMe₂ SO₂Me 4-81 NO₂ NMe₂ SO₂Et 4-82 NO₂ NH₂ 1H-1,2,4-triazol- 1-yl 4-83 NO₂ NHMe 1H-1,2,4-triazol- 1-yl 4-84 NO₂ NMe₂ 1H-1,2,4-triazol- 1-yl 4-85 Me SMe H 4-86 Me SOMe H 4-87 Me SO₂Me H 4-88 Me SEt H 4-89 Me SOEt H 4-90 Me SO₂Et H 4-91 Me S(CH₂)₂OMe H 4-92 Me SO(CH₂)₂OMe H 4-93 Me SO₂(CH₂)₂OMe H 4-94 Me F F 4-95 Me F Cl 4-96 Me SEt F 4-97 Me SOEt F 4-98 Me SO₂Et F 4-99 Me Me Cl 4-100 Me F Cl 4-101 Me Cl Cl 4-102 Me NH₂ Cl 4-103 Me NHMe Cl 4-104 Me NMe₂ Cl 4-105 Me O(CH₂)₂OMe Cl 4-106 Me O(CH₂)₃OMe Cl 4-107 Me O(CH₂)₄OMe Cl 4-108 Me OCH₂CONMe₂ Cl 4-109 Me O(CH₂)₂—CO—NMe₂ Cl 4-110 Me O(CH₂)₂—NH(CO)NMe₂ Cl 4-111 Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 4-112 Me O(CH₂)₂—NHCO₂Me Cl 4-113 Me OCH₂—NHSO₂cPr Cl 4-114 Me O(CH₂)-5-2,4-dimethyl- Cl 2,4-dihydro-3H-1,2,4- triazol-3-one 4-115 Me O(CH₂)-3,5-dimethyl- Cl 1,2-oxazol-4-yl 4-116 Me SMe Cl 4-117 Me SOMe Cl 4-118 Me SO₂Me Cl 4-119 Me SEt Cl 4-120 Me SOEt Cl 4-121 Me SO₂Et Cl 4-122 Me S(CH₂)₂OMe Cl 4-123 Me SO(CH₂)₂OMe Cl 4-124 Me SO₂(CH₂)₂OMe Cl 4-125 Me NH₂ Br 4-126 Me NHMe Br 4-127 Me NMe₂ Br 4-128 Me OCH₂(CO)NMe₂ Br 4-129 Me O(CH₂)-5-pyrrolidin-2-one Br 4-130 Me SMe Br 4-131 Me SOMe Br 4-132 Me SO₂Me Br 4-133 Me SEt Br 4-134 Me SOEt Br 4-135 Me SO₂Et Br 4-136 Me SMe I 4-137 Me SOMe I 4-138 Me SO₂Me I 4-139 Me SEt I 4-140 Me SOEt I 4-141 Me SO₂Et I 4-142 Me Cl CF₃ 4-143 Me SMe CF₃ 4-144 Me SOMe CF₃ 4-145 Me SO₂Me CF₃ 4-146 Me SEt CF₃ 4-147 Me SOEt CF₃ 4-148 Me SO₂Et CF₃ 4-149 Me S(CH₂)₂OMe CF₃ 4-150 Me SO(CH₂)₂OMe CF₃ 4-151 Me SO₂(CH₂)₂OMe CF₃ 4-152 Me Me SO₂Me 4-153 Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 4-154 Me 4,5-dihydro-1,2-oxazol- SO₂Et 3-yl 4-155 Me 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol-3-yl 4-156 Me 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 4-157 Me NH₂ SO₂Me 4-158 Me NHMe SO₂Me 4-159 Me NMe₂ SO₂Me 4-160 Me NH(CH₂)₂OMe SO₂Me 4-161 Me pyrazol-1-yl SO₂Me 4-162 Me OH SO₂Me 4-163 Me OMe SO₂Me 4-164 Me OMe SO₂Et 4-165 Me OEt SO₂Me 4-166 Me OEt SO₂Et 4-167 Me OiPr SO₂Me 4-168 Me OiPr SO₂Et 4-169 Me O(CH₂)₂OMe SO₂Me 4-170 Me O(CH₂)₂OMe SO₂Et 4-171 Me O(CH₂)₃OMe SO₂Me 4-172 Me O(CH₂)₃OMe SO₂Et 4-173 Me O(CH₂)₄OMe SO₂Me 4-174 Me O(CH₂)₄OMe SO₂Et 4-175 Me O(CH₂)₂NHSO2Me SO₂Me 4-176 Me O(CH₂)₂NHSO2Me SO₂Et 4-177 Me OCH₂(CO)NMe₂ SO₂Me 4-178 Me OCH₂(CO)NMe₂ SO₂Et 4-179 Me [1,4]dioxan-2- SO₂Me ylmethoxy 4-180 Me [1,4]dioxan-2- SO₂Et ylmethoxy 4-181 Me O(CH₂)₂—O-(3,5-di- SO₂Me methoxypyrimidin-2-yl) 4-182 Me Cl SO₂Me 4-183 Me SMe SO₂Me 4-184 Me SOMe SO₂Me 4-185 Me SO₂Me SO₂Me 4-186 Me SO₂Me SO₂Et 4-187 Me SEt SO₂Me 4-188 Me SOEt SO₂Me 4-189 Me SO₂Et SO₂Me 4-190 Me S(CH₂)₂OMe SO₂Me 4-191 Me SO(CH₂)₂OMe SO₂Me 4-192 Me SO₂(CH₂)₂OMe SO2Me 4-193 CH₂SMe OMe SO₂Me 4-194 CH₂OMe OMe SO₂Me 4-195 CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 4-196 CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂Me 4-197 CH₂O(CH₂)₃OMe OMe SO₂Me 4-198 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me 4-199 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 4-200 Et SMe Cl 4-201 Et SO₂Me Cl 4-202 Et SMe CF₃ 4-203 Et SO₂Me CF₃ 4-204 Et F SO₂Me 4-205 Et NH(CH₂)₂OMe SO₂Me 4-206 iPr SO₂Me CF₃ 4-207 cPr SO₂Me CF₃ 4-208 CF₃ O(CH₂)₂OMe F 4-209 CF₃ O(CH₂)₃OMe F 4-210 CF₃ OCH₂CONMe₂ F 4-211 CF₃ [1,4]dioxan-2- F ylmethoxy 4-212 CF₃ O(CH₂)₂OMe Cl 4-213 CF₃ O(CH₂)₃OMe Cl 4-214 CF₃ OCH₂CONMe₂ Cl 4-215 CF₃ [1,4]dioxan-2- Cl ylmethoxy 4-216 CF₃ O(CH₂)₂OMe Br 4-217 CF₃ O(CH₂)₃OMe Br 4-218 CF₃ OCH₂CONMe₂ Br 4-219 CF₃ [1,4]dioxan-2- Br ylmethoxy 4-220 CF₃ O(CH₂)₂OMe I 4-221 CF₃ O(CH₂)₃OMe I 4-222 CF₃ OCH₂CONMe₂ I 4-223 CF₃ [1,4]dioxan-2- I ylmethoxy 4-224 CF₃ F SO₂Me 4-225 CF₃ F SO₂Et 4-226 CF₃ O(CH₂)₂OMe SO₂Me 4-227 CF₃ O(CH₂)₂OMe SO₂Et 4-228 CF₃ O(CH₂)₃OMe SO₂Me 4-229 CF₃ O(CH₂)₃OMe SO₂Et 4-230 CF₃ OCH₂CONMe₂ SO₂Me 4-231 CF₃ OCH₂CONMe₂ SO₂Et 4-232 CF₃ [1,4]dioxan-2- SO₂Me ylmethoxy 4-233 CF₃ [1,4]dioxan-2- SO₂Et ylmethoxy 4-234 F SMe CF₃ 4-235 F SOMe CF₃ 4-236 Cl Me Cl 4-237 Cl OCH₂CHCH₂ Cl 4-238 Cl OCH₂CHF₂ Cl 4-239 Cl O(CH₂)₂OMe Cl 4-240 Cl OCH₂CONMe₂ Cl 4-241 Cl O(CH₂)-5-pyrrolidin-2- Cl one 4-242 Cl SMe Cl 4-243 Cl SOMe Cl 4-244 Cl SO₂Me Cl 4-245 Cl F SMe 4-246 Cl Cl SO₂Me 4-247 Cl COOMe SO₂Me 4-248 Cl CONMe₂ SO₂Me 4-249 Cl CONMe(OMe) SO₂Me 4-250 Cl CH₂OMe SO₂Me 4-251 Cl CH₂OMe SO₂Et 4-252 Cl CH₂OEt SO₂Me 4-253 Cl CH₂OEt SO₂Et 4-254 Cl CH₂OCH₂CHF₂ SO₂Me 4-255 Cl CH₂OCH₂CF₃ SO₂Me 4-256 Cl CH₂OCH₂CF₃ SMe 4-257 Cl CH₂OCH₂CF₃ SO₂Et 4-258 Cl CH₂OCH₂CF₂CHF₂ SO₂Me 4-259 Cl CH₂O-c-pentyl SO₂Me 4-260 Cl CH₂PO(OMe)₂ SO₂Me 4-261 Cl 4,5-dihydro-1,2-oxazol- SMe 3-yl 4-262 Cl 4,5-dihydro-1,2-oxazol- SO₂Me 3-yl 4-263 Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 4-264 Cl 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol-3-yl 4-265 Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 4-266 Cl 5-(methoxymethyl)-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 4-267 Cl 5-(methoxymethyl)-5- SO₂Et methy1-4,5-dihydro-1,2- oxazol-3-yl 4-268 Cl CH₂O-tetrahydrofuran- SO₂Me 3-yl 4-269 Cl CH₂O-tetrahydrofuran- SO₂Et 3-yl 4-270 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 4-271 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-2-yl 4-272 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-3-yl 4-273 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-3-yl 4-274 Cl OMe SO₂Me 4-275 Cl OMe SO₂Et 4-276 Cl OEt SO₂Me 4-277 Cl OEt SO₂Et 4-278 Cl OiPr SO₂Me 4-279 Cl OiPr SO₂Et 4-280 Cl O(CH₂)₂OMe SO₂Me 4-281 Cl O(CH₂)₄OMe SO₂Me 4-282 Cl O(CH₂)₄OMe SO₂Et 4-283 Cl O(CH₂)₃OMe SO₂Me 4-284 Cl O(CH₂)₃OMe SO₂Et 4-285 Cl O(CH₂)₂OMe SO₂Me 4-286 Cl O(CH₂)₂OMe SO₂Et 4-287 Cl [1,4]dioxan-2- SO₂Me ylmethoxy 4-288 Cl [1,4]dioxan-2- SO₂Et ylmethoxy 4-289 Cl OCH₂(CO)NMe₂ SO₂Me 4-290 Cl OCH₂(CO)NMe₂ SO₂Et 4-291 Cl SMe SO₂Me 4-292 Cl SOMe SO₂Me 4-293 Br OMe Br 4-294 Br O(CH₂)₂OMe Br 4-295 Br O(CH₂)₂OMe SO₂Me 4-296 Br O(CH₂)₂OMe SO₂Et 4-297 Br O(CH₂)₃OMe SO₂Me 4-298 Br O(CH₂)₃OMe SO₂Et 4-299 Br O(CH₂)₄OMe SO₂Me 4-300 Br O(CH₂)₄OMe SO₂Et 4-301 Br [1,4]dioxan-2- SO₂Me ylmethoxy 4-302 Br [1,4]dioxan-2- SO₂Et ylmethoxy 4-303 I O(CH₂)₂OMe SO₂Me 4-304 I O(CH₂)₂OMe SO₂Et 4-305 I O(CH₂)₃OMe SO₂Me 4-306 I O(CH₂)₃OMe SO₂Et 4-307 I O(CH₂)₄OMe SO₂Me 4-308 I O(CH₂)₄OMe SO₂Et 4-309 I [1,4]dioxan-2- SO₂Me ylmethoxy 4-310 I [1,4]dioxan-2- SO₂Et ylmethoxy 4-311 OMe SMe CF₃ 4-312 OMe SOMe CF₃ 4-313 OMe SO₂Me CF₃ 4-314 OMe SOEt CF₃ 4-315 OMe SO₂Et CF₃ 4-316 OMe S(CH₂)₂OMe CF₃ 4-317 OMe SO(CH₂)₂OMe CF₃ 4-318 OMe SO₂(CH₂)₂OMe CF₃ 4-319 OMe SMe Cl 4-320 OMe SOMe Cl 4-321 OMe SO₂Me Cl 4-322 OMe SEt Cl 4-323 OMe SOEt Cl 4-324 OMe SO2Et Cl 4-325 OMe S(CH₂)₂OMe Cl 4-326 OMe SO(CH₂)₂OMe Cl 4-327 OMe SO₂(CH₂)₂OMe Cl 4-328 OCH₂c-Pr SMe CF₃ 4-329 OCH₂c-Pr SOMe CF₃ 4-330 OCH₂c-Pr SO₂Me CF₃ 4-331 OCH₂c-Pr SEt CF₃ 4-332 OCH₂c-Pr SOEt CF₃ 4-333 OCH₂c-Pr SO₂Et CF₃ 4-334 OCH₂c-Pr S(CH₂)₂OMe CF₃ 4-335 OCH₂c-Pr SO(CH₂)₂OMe CF₃ 4-336 OCH₂c-Pr SO₂(CH₂)₂OMe CF₃ 4-337 OCH₂c-Pr SMe Cl 4-338 OCH₂c-Pr SOMe Cl 4-339 OCH₂c-Pr SO₂Me Cl 4-340 OCH₂c-Pr SEt Cl 4-341 OCH₂c-Pr SOEt Cl 4-342 OCH₂c-Pr SO₂Et Cl 4-343 OCH₂c-Pr S(CH₂)₂OMe Cl 4-344 OCH₂c-Pr SO(CH₂)₂OMe Cl 4-345 OCH₂c-Pr SO₂(CH₂)₂OMe Cl 4-346 OCH₂c-Pr SMe SO₂Me 4-347 OCH₂c-Pr SOMe SO₂Me 4-348 OCH₂c-Pr SO₂Me SO₂Me 4-349 OCH₂c-Pr SEt SO₂Me 4-350 OCH₂c-Pr SOEt SO₂Me 4-351 OCH₂c-Pr SO₂Et SO₂Me 4-352 OCH₂c-Pr S(CH₂)₂OMe SO₂Me 4-353 OCH₂c-Pr SO(CH₂)₂OMe SO₂Me 4-354 OCH₂c-Pr SO₂(CH₂)₂OMe SO₂Me 4-355 SO₂Me F CF₃ 4-356 SO₂Me NH₂ CF₃ 4-357 SO₂Me NHEt Cl 4-358 SMe SEt F 4-359 SMe SMe F 4-360 Cl SMe CF₃ 4-361 Cl S(O)Me CF₃ 4-362 Cl SO₂Me CF₃ 4-363 Cl SO₂Me SO₂Me

TABLE 5 Compounds of the general formula (I) in which A represents CY, V represents hydrogen, W represents fluorine and R represents CH₂OMe

Physical data (¹H-NMR, DMSO-d₆, No. X Y Z 400 MHz) 5-1 F H Cl 5-2 F H SO₂Me 5-3 F H SO₂Et 5-4 F H CF₃ 5-5 F H NO₂ 5-6 Cl H Br 5-7 Cl H SMe 5-8 Cl H SOMe 5-9 Cl H SO₂Me 5-10 Cl H SO₂CH₂Cl 5-11 Cl H SEt 5-12 Cl H SO₂Et 5-13 Cl H CF₃ 5-14 Cl H NO₂ 5-15 Cl H pyrazol-1-yl 5-16 Cl H 1H-1,2,4-triazol-1- yl 5-17 Br H Cl 5-18 Br H Br 5-19 Br H SO₂Me 5-20 Br H SO₂Et 5-21 Br H CF₃ 5-22 SO₂Me H Cl 5-23 SO₂Me H Br 5-24 SO₂Me H SMe 5-25 SO₂Me H SOMe 5-26 SO₂Me H SO₂Me 5-27 SO₂Me H SO₂Et 5-28 SO₂Me H CF₃ 5-29 SO₂Et H Cl 5-30 SO₂Et H Br 5-31 SO₂Et H SMe 5-32 SO₂Et H SOMe 5-33 SO₂Et H SO₂Me 5-34 SO₂Et H CF₃ 5-35 NO₂ H F 5-36 NO₂ H Cl 5-37 NO₂ H Br 5-38 NO₂ H I 5-39 NO₂ H CN 5-40 NO₂ H SO₂Me 5-41 NO₂ H SO₂Et 5-42 NO₂ H CF₃ 5-43 Me H Cl 5-44 Me H Br 5-45 Me H SMe 5-46 Me H SO₂Me 5-47 Me H SO₂CH₂Cl 5-48 Me H SEt 5-49 Me H SO₂Et 5-50 Me H CF₃ 5-51 CH₂SO₂Me H CF₃ 5-52 Et H Cl 5-53 Et H Br 5-54 Et H SMe 5-55 Et H SO₂Me 5-56 Et H SO₂CH₂Cl 5-57 Et H SEt 5-58 Et H SO₂Et 5-59 Et H CF₃ 5-60 CF₃ H Cl 5-61 CF₃ H Br 5-62 CF₃ H SO₂Me 5-63 CF₃ H SO₂Et 5-64 CF₃ H CF₃ 5-65 NO₂ NH₂ F 5-66 NO₂ NHMe F 5-67 NO₂ NMe₂ F 5-68 NO₂ Me Cl 5-69 NO₂ NH₂ Cl 5-70 NO₂ NHMe Cl 5-71 NO₂ NMe₂ Cl 5-72 NO₂ NH₂ Br 5-73 NO₂ NHMe Br 5-74 NO₂ NMe₂ Br 5-75 NO₂ NH₂ CF₃ 5-76 NO₂ NMe₂ CF₃ 5-77 NO₂ NH₂ SO₂Me 5-78 NO₂ NH₂ SO₂Et 5-79 NO₂ NHMe SO₂Me 5-80 NO₂ NMe₂ SO₂Me 5-81 NO₂ NMe₂ SO₂Et 5-82 NO₂ NH₂ 1H-1,2,4-triazol-1- yl 5-83 NO₂ NHMe 1H-1,2,4-triazol-1- yl 5-84 NO₂ NMe₂ 1H-1,2,4-triazol-1- yl 5-85 Me SMe H 5-86 Me SOMe H 5-87 Me SO₂Me H 5-88 Me SEt H 5-89 Me SOEt H 5-90 Me SO₂Et H 5-91 Me S(CH₂)₂OMe H 5-92 Me SO(CH₂)₂OMe H 5-93 Me SO₂(CH₂)₂OMe H 5-94 Me F F 5-95 Me F Cl 5-96 Me SEt F 5-97 Me SOEt F 5-98 Me SO₂Et F 5-99 Me Me Cl 5-100 Me F Cl 5-101 Me Cl Cl 5-102 Me NH₂ Cl 5-103 Me NHMe Cl 5-104 Me NMe₂ Cl 5-105 Me O(CH₂)₂OMe Cl 5-106 Me O(CH₂)₃OMe Cl 5-107 Me O(CH₂)₄OMe Cl 5-108 Me OCH₂CONMe₂ Cl 5-109 Me O(CH₂)₂—CO—NMe₂ Cl 5-110 Me O(CH₂)₂—NH(CO)NMe₂ Cl 5-111 Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 5-112 Me O(CH₂)₂—NHCO₂Me Cl 5-113 Me OCH₂—NHSO₂cPr Cl 5-114 Me O(CH₂)-5-2,4-dimethyl- Cl 2,4-dihydro-3H-1,2,4-triazol-3-one 5-115 Me O(CH₂)-3,5-dimethyl- Cl 1,2-oxazol-4-yl 5-116 Me SMe Cl 5-117 Me SOMe Cl 5-118 Me SO₂Me Cl 5-119 Me SEt Cl 5-120 Me SOEt Cl 5-121 Me SO₂Et Cl 5-122 Me S(CH₂)₂OMe Cl 5-123 Me SO(CH₂)₂OMe Cl 5-124 Me SO₂(CH₂)₂OMe Cl 5-125 Me NH₂ Br 5-126 Me NHMe Br 5-127 Me NMe₂ Br 5-128 Me OCH₂(CO)NMe₂ Br 5-129 Me O(CH₂)-5-pyrrolidin-2- Br one 5-130 Me SMe Br 5-131 Me SOMe Br 5-132 Me SO₂Me Br 5-133 Me SEt Br 5-134 Me SOEt Br 5-135 Me SO₂Et Br 5-136 Me SMe I 5-137 Me SOMe I 5-138 Me SO₂Me I 5-139 Me SEt I 5-140 Me SOEt I 5-141 Me SO₂Et I 5-142 Me Cl CF₃ 5-143 Me SMe CF₃ 5-144 Me SOMe CF₃ 5-145 Me SO₂Me CF₃ 5-146 Me SEt CF₃ 5-147 Me SOEt CF₃ 5-148 Me SO₂Et CF₃ 5-149 Me S(CH₂)₂OMe CF₃ 5-150 Me SO(CH₂)₂OMe CF₃ 5-151 Me SO₂(CH₂)₂OMe CF₃ 5-152 Me Me SO₂Me 5-153 Me 4,5-dihydro-1,2-oxazol- SO₂Me 3-yl 5-154 Me 4,5-dihydro-1,2-oxazol- SO₂Et 3-yl 5-155 Me 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol-3-yl 5-156 Me 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 5-157 Me NH₂ SO₂Me 5-158 Me NHMe SO₂Me 5-159 Me NMe₂ SO₂Me 5-160 Me NH(CH₂)₂OMe SO₂Me 5-161 Me pyrazol-1-yl SO₂Me 5-162 Me OH SO₂Me 5-163 Me OMe SO₂Me 5-164 Me OMe SO₂Et 5-165 Me OEt SO₂Me 5-166 Me OEt SO₂Et 5-167 Me OiPr SO₂Me 5-168 Me OiPr SO₂Et 5-169 Me O(CH₂)₂OMe SO₂Me 5-170 Me O(CH₂)₂OMe SO₂Et 5-171 Me O(CH₂)₃OMe SO₂Me 5-172 Me O(CH₂)₃OMe SO₂Et 5-173 Me O(CH₂)₄OMe SO₂Me 5-174 Me O(CH₂)₄OMe SO₂Et 5-175 Me O(CH₂)₂NHSO2Me SO₂Me 5-176 Me O(CH₂)₂NHSO2Me SO₂Et 5-177 Me OCH₂(CO)NMe₂ SO₂Me 5-178 Me OCH₂(CO)NMe₂ SO₂Et 5-179 Me [1,4]dioxan-2- SO₂Me ylmethoxy 5-180 Me [1,4]dioxan-2- SO₂Et ylmethoxy 5-181 Me O(CH₂)₂—O-(3,5-di- SO₂Me methoxypyrimidin-2-yl) 5-182 Me Cl SO₂Me 5-183 Me SMe SO₂Me 5-184 Me SOMe SO₂Me 5-185 Me SO₂Me SO₂Me 5-186 Me SO₂Me SO₂Et 5-187 Me SEt SO₂Me 5-188 Me SOEt SO₂Me 5-189 Me SO₂Et SO₂Me 5-190 Me S(CH₂)₂OMe SO₂Me 5-191 Me SO(CH₂)₂OMe SO₂Me 5-192 Me SO₂(CH₂)₂OMe SO₂Me 5-193 CH₂SMe OMe SO₂Me 5-194 CH₂OMe OMe SO₂Me 5-195 CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 5-196 CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂Me 5-197 CH₂O(CH₂)₃OMe OMe SO₂Me 5-198 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me 5-199 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 5-200 Et SMe Cl 5-201 Et SO₂Me Cl 5-202 Et SMe CF₃ 5-203 Et SO₂Me CF₃ 5-204 Et F SO₂Me 5-205 Et NH(CH₂)₂OMe SO₂Me 5-206 iPr SO₂Me CF₃ 5-207 cPr SO₂Me CF₃ 5-208 CF₃ O(CH₂)₂OMe F 5-209 CF₃ O(CH₂)₃OMe F 5-210 CF₃ OCH₂CONMe₂ F 5-211 CF₃ [1,4]dioxan-2-ylmethoxy F 5-212 CF₃ O(CH₂)₂OMe Cl 5-213 CF₃ O(CH₂)₃OMe Cl 5-214 CF₃ OCH₂CONMe₂ Cl 5-215 CF₃ [1,4]dioxan-2-ylmethoxy Cl 5-216 CF₃ O(CH₂)₂OMe Br 5-217 CF₃ O(CH₂)₃OMe Br 5-218 CF₃ OCH₂CONMe₂ Br 5-219 CF₃ [1,4]dioxan-2-ylmethoxy Br 5-220 CF₃ O(CH₂)₂OMe I 5-221 CF₃ O(CH₂)₃OMe I 5-222 CF₃ OCH₂CONMe₂ I 5-223 CF₃ [1,4]dioxan-2-ylmethoxy I 5-224 CF₃ F SO₂Me 5-225 CF₃ F SO₂Et 5-226 CF₃ O(CH₂)₂OMe SO₂Me 5-227 CF₃ O(CH₂)₂OMe SO₂Et 5-228 CF₃ O(CH₂)₃OMe SO₂Me 5-229 CF₃ O(CH₂)₃OMe SO₂Et 5-230 CF₃ OCH₂CONMe₂ SO₂Me 5-231 CF₃ OCH₂CONMe₂ SO₂Et 5-232 CF₃ [1,4]dioxan-2-ylmethoxy SO₂Me 5-233 CF₃ [1,4]dioxan-2-ylmethoxy SO₂Et 5-234 F SMe CF₃ 5-235 F SOMe CF₃ 5-236 Cl Me Cl 5-237 Cl OCH₂CHCH₂ Cl 5-238 Cl OCH₂CHF₂ Cl 5-239 Cl O(CH₂)₂OMe Cl 5-240 Cl OCH₂CONMe₂ Cl 5-241 Cl O(CH₂)-5-pyrrolidin-2-one Cl 5-242 Cl SMe Cl 5-243 Cl SOMe Cl 5-244 Cl SO₂Me Cl 5-245 Cl F SMe 5-246 Cl Cl SO₂Me 5-247 Cl COOMe SO₂Me 5-248 Cl CONMe₂ SO₂Me 5-249 Cl CONMe(OMe) SO₂Me 5-250 Cl CH₂OMe SO₂Me 5-251 Cl CH₂OMe SO₂Et 5-252 Cl CH₂OEt SO₂Me 5-253 Cl CH₂OEt SO₂Et 5-254 Cl CH₂OCH₂CHF₂ SO₂Me 5-255 Cl CH₂OCH₂CF₃ SO₂Me 5-256 Cl CH₂OCH₂CF₃ SO₂Et 5-257 Cl CH₂OCH₂CF₂CHF₂ SO₂Me 5-258 Cl CH₂O-c-pentyl SO₂Me 5-259 Cl CH₂PO(OMe)₂ SO₂Me 5-260 Cl 4,5-dihydro-1,2-oxazol-3-yl SMe 5-261 Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Me 5-262 Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 5-263 Cl 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol-3-yl 5-264 Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 5-265 Cl 5-(methoxymethyl)-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 5-266 Cl 5-(methoxymethyl)-5- SO₂Et methy1-4,5-dihydro-1,2-oxazol-3-yl 5-267 Cl CH₂O-tetrahydrofuran-3-yl SO₂Me 5-268 Cl CH₂O-tetrahydrofuran-3-yl SO₂Et 5-269 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 5-270 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-2-yl 5-271 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-3-yl 5-272 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-3-yl 5-273 Cl OMe SO₂Me 5-274 Cl OMe SO₂Et 5-275 Cl OEt SO₂Me 5-276 Cl OEt SO₂Et 5-277 Cl OiPr SO₂Me 5-278 Cl OiPr SO₂Et 5-279 Cl O(CH₂)₂OMe SO₂Me 5-280 Cl O(CH₂)₄OMe SO₂Me 5-281 Cl O(CH₂)₄OMe SO₂Et 5-282 Cl O(CH₂)₃OMe SO₂Me 5-283 Cl O(CH₂)₃OMe SO₂Et 5-284 Cl O(CH₂)₂OMe SO₂Me 5-285 Cl O(CH₂)₂OMe SO₂Et 5-286 Cl [1,4]dioxan-2-ylmethoxy SO₂Me 5-287 Cl [1,4]dioxan-2-ylmethoxy SO₂Et 5-288 Cl OCH₂(CO)NMe₂ SO₂Me 5-289 Cl OCH₂(CO)NMe₂ SO₂Et 5-290 Cl SMe SO₂Me 5-291 Cl SOMe SO₂Me 5-292 Br OMe Br 5-293 Br O(CH₂)₂OMe Br 5-294 Br O(CH₂)₂OMe SO₂Me 5-295 Br O(CH₂)₂OMe SO₂Et 5-296 Br O(CH₂)₃OMe SO₂Me 5-297 Br O(CH₂)₃OMe SO₂Et 5-298 Br O(CH₂)₄OMe SO₂Me 5-299 Br O(CH₂)₄OMe SO₂Et 5-300 Br [1,4]dioxan-2-ylmethoxy SO₂Me 5-301 Br [1,4]dioxan-2-ylmethoxy SO₂Et 5-302 I O(CH₂)₂OMe SO₂Me 5-303 I O(CH₂)₂OMe SO₂Et 5-304 I O(CH₂)₃OMe SO₂Me 5-305 I O(CH₂)₃OMe SO₂Et 5-306 I O(CH₂)₄OMe SO₂Me 5-307 I O(CH₂)₄OMe SO₂Et 5-308 I [1,4]dioxan-2-ylmethoxy SO₂Me 5-309 I [1,4]dioxan-2-ylmethoxy SO₂Et 5-310 OMe SMe CF₃ 5-311 OMe SOMe CF₃ 5-312 OMe SO₂Me CF₃ 5-313 OMe SOEt CF₃ 5-314 OMe SO₂Et CF₃ 5-315 OMe S(CH₂)₂OMe CF₃ 5-316 OMe SO(CH₂)₂OMe CF₃ 5-317 OMe SO₂(CH₂)₂OMe CF₃ 5-318 OMe SMe Cl 5-319 OMe SOMe Cl 5-320 OMe SO₂Me Cl 5-321 OMe SEt Cl 5-322 OMe SOEt Cl 5-323 OMe SO2Et Cl 5-324 OMe S(CH₂)₂OMe Cl 5-325 OMe SO(CH₂)₂OMe Cl 5-326 OMe SO₂(CH₂)₂OMe Cl 5-327 OMe H SO₂Me 5-328 OCH₂-c-Pr SMe CF₃ 5-329 OCH₂-c-Pr SOMe CF₃ 5-330 OCH₂-c-Pr SO₂Me CF₃ 5-331 OCH₂-c-Pr SEt CF₃ 5-332 OCH₂-c-Pr SOEt CF₃ 5-333 OCH₂-c-Pr SO₂Et CF₃ 5-334 OCH₂-c-Pr S(CH₂)₂OMe CF₃ 5-335 OCH₂-c-Pr SO(CH₂)₂OMe CF₃ 5-336 OCH₂-c-Pr SO₂(CH₂)₂OMe CF₃ 5-337 OCH₂-c-Pr SMe Cl 5-338 OCH₂-c-Pr SOMe Cl 5-339 OCH₂-c-Pr SO₂Me Cl 5-340 OCH₂-c-Pr SEt Cl 5-341 OCH₂-c-Pr SOEt Cl 5-342 OCH₂-c-Pr SO₂Et Cl 5-343 OCH₂-c-Pr S(CH₂)₂OMe Cl 5-344 OCH₂-c-Pr SO(CH₂)₂OMe Cl 5-345 OCH₂-c-Pr SO₂(CH₂)₂OMe Cl 5-346 OCH₂-c-Pr SMe SO₂Me 5-347 OCH₂-c-Pr SOMe SO₂Me 5-348 OCH₂-c-Pr SO₂Me SO₂Me 5-349 OCH₂-c-Pr SEt SO₂Me 5-350 OCH₂-c-Pr SOEt SO₂Me 5-351 OCH₂-c-Pr SO₂Et SO₂Me 5-352 OCH₂-c-Pr S(CH₂)₂OMe SO₂Me 5-353 OCH₂-c-Pr SO(CH₂)₂OMe SO₂Me 5-354 OCH₂-c-Pr SO₂(CH₂)₂OMe SO₂Me 5-355 SO₂Me F CF₃ 5-356 SO₂Me NH₂ CF₃ 5-357 SO₂Me NHEt Cl 5-358 SMe SEt F 5-359 SMe SMe F 5-360 F SO₂Me CF₃ 5-361 Cl SMe CF₃ 5-362 Cl S(O)Me CF₃ 5-363 Cl SO₂Me CF₃ 5-364 Cl SO₂Me SO₂Me

TABLE 6 Compounds of the general formula (I) in which A represents CY, V represents hydrogen, W represents fluorine

No. R X Y Z Physical data 6-1 c-Pr NO₂ H SO₂Me 6-2 c-Pr Cl H SO₂Me 6-3 c-Pr SO₂Me H CF₃ 6-4 c-Pr NO₂ H OMe 6-5 c-Pr NO₂ H Br 6-6 c-Pr NO₂ H Cl 6-7 c-Pr NO₂ H CF₃ 6-8 c-Pr NO₂ H NO₂ 6-9 c-Pr NO₂ H Me 6-10 c-Pr NO₂ H F 6-11 c-Pr OMe H SO₂Me 6-12 c-Pr CF₃ H NO₂ 6-13 c-Pr CF₃ H Cl 6-14 c-Pr CH₂SO₂Me H Br 6-15 c-Pr Cl CH₂OCH₂CF₃ SO₂Me 6-16 c-Pr Cl CH₂OCH₂CF₃ SMe 6-17 c-Pr Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-18 c-Pr Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-19 c-Pr Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-20 c-Pr Cl SMe Cl 6-21 c-Pr Cl SMe SO₂Me 6-22 c-Pr Cl Me SO₂Et 6-23 c-Pr Cl O(CH₂)₂OMe Cl 6-24 c-Pr Cl OCH₂- Cl cyclopropyl 6-25 c-Pr Cl OMe Cl 6-26 c-Pr Cl NHAc Cl 6-27 c-Pr Cl OCH₂C(O)NMe₂ Cl 6-28 c-Pr Cl Cl SO₂Me 6-29 c-Pr Cl pyrazol-1-yl SO₂Me 6-30 c-Pr Cl 4-methoxypyrazol-1-yl SO₂Me 6-31 c-Pr Cl 1,2,3-triazol-1-yl SO₂Me 6-32 c-Pr Cl 1,2,3-triazol-2-yl SO₂Me 6-33 c-Pr Cl F SO₂Me 6-34 c-Pr Me SO₂Me SO₂Me 6-35 c-Pr Me SO₂Me CF₃ 6-36 c-Pr Me NMe₂ SO₂Me 6-37 c-Pr Me S(O)Me CF₃ 6-38 c-Pr Me SMe CF₃ 6-39 c-Pr Me SO₂CH₂CH₂OMe CF₃ 6-40 c-Pr Me pyrazol-1-yl SO₂Me 6-41 c-Pr Me 4-methoxypyrazol-1-yl SO₂Me 6-42 c-Pr Me 1,2,3-triazol-1-yl SO₂Me 6-43 c-Pr Me 1,2,3-triazol-2-yl SO₂Me 6-44 c-Pr Me Cl SO₂Me 6-45 c-Pr Me Me SO₂Me 6-46 c-Pr Me F Cl 6-47 c-Pr Me SO₂Me Cl 6-48 c-Pr Me NMe₂ SO₂Me 6-49 c-Pr Me NH(CH₂)₂OMe SO₂Me 6-50 c-Pr CF₃ F SO₂CH₃ 6-51 c-Pr CF₃ SMe SO₂CH₃ 6-52 c-Pr CF₃ SEt SO₂CH₃ 6-53 c-Pr CF₃ S(O)Et SO₂CH₃ 6-54 c-Pr CF₃ SO₂CH₃ SO₂CH₃ 6-55 c-Pr CF₃ OCH₂CH₂OMe SO₂CH₃ 6-56 c-Pr CF₃ OCH₂(CO)NMe₂ SO2Me 6-57 c-Pr CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-58 c-Pr SMe SMe F 6-59 c-Pr SMe SEt F 6-60 c-Pr SO₂CH₃ F Cl 6-61 c-Pr F S(O)Me CF₃ 6-62 c-Pr F SMe CF₃ 6-63 CO₂Et NO₂ H SO₂Me 6-64 CO₂Et Cl H SO₂Me 6-65 CO₂Et SO₂Me H CF₃ 6-66 CO₂Et NO₂ H OMe 6-67 CO₂Et NO₂ H Br 6-68 CO₂Et NO₂ H CF₃ 6-69 CO₂Et NO₂ H NO₂ 6-70 CO₂Et NO₂ H Cl 6-71 CO₂Et NO₂ H Me 6-72 CO₂Et NO₂ H F 6-73 CO₂Et OMe H SO₂Me 6-74 CO₂Et CF₃ H NO₂ 6-75 CO₂Et CH₂SO₂Me H Br 6-76 CO₂Et Cl CH₂OCH₂CF₃ SO₂Me 6-77 CO₂Et Cl CH₂OCH₂CF₃ SMe 6-78 CO₂Et Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 6-79 CO₂Et Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-80 CO₂Et Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-81 CO₂Et Cl SMe Cl 6-82 CO₂Et Cl SMe SO₂Me 6-83 CO₂Et Cl Me SO₂Et 6-84 CO₂Et Cl O(CH₂)₂OMe Cl 6-85 CO₂Et Cl OCH₂-cyclopropyl Cl 6-86 CO₂Et Cl OMe Cl 6-87 CO₂Et Cl NHAc Cl 6-88 CO₂Et Cl OCH₂C(O)NMe₂ Cl 6-89 CO₂Et Cl Cl SO₂Me 6-90 CO₂Et Cl pyrazol-1-yl SO₂Me 6-91 CO₂Et Cl 4-methoxypyrazol-1-yl SO₂Me 6-92 CO₂Et Cl 1,2,3-triazol-1-yl SO₂Me 6-93 CO₂Et Cl 1,2,3-triazol-2-yl SO₂Me 6-94 CO₂Et Cl F SO₂Me 6-95 CO₂Et Me SO₂Me SO₂Me 6-96 CO₂Et Me SO₂Me CF₃ 6-97 CO₂Et Me NMe₂ SO₂Me 6-98 CO₂Et Me S(O)Me CF₃ 6-99 CO₂Et Me SMe CF₃ 6-100 CO₂Et Me SO₂CH₂CH₂OMe CF₃ 6-101 CO₂Et Me pyrazol-1-yl SO₂Me 6-102 CO₂Et Me 4-methoxypyrazol-1-yl SO₂Me 6-103 CO₂Et Me 1,2,3-triazol-1-yl SO₂Me 6-104 CO₂Et Me 1,2,3-triazol-2-yl SO₂Me 6-105 CO₂Et Me Cl SO₂Me 6-106 CO₂Et Me Me SO₂Me 6-107 CO₂Et Me Me SMe 6-108 CO₂Et Me SO₂Me Cl 6-109 CO₂Et Me NMe₂ SO₂Me 6-110 CO₂Et Me NH(CH₂)₂OMe SO₂Me 6-111 CO₂Et CF₃ F SO₂CH₃ 6-112 CO₂Et CF₃ SMe SO₂CH₃ 6-113 CO₂Et CF₃ SEt SO₂CH₃ 6-114 CO₂Et CF₃ S(O)Et SO₂CH₃ 6-115 CO₂Et CF₃ SO₂CH₃ SO₂CH₃ 6-116 CO₂Et CF₃ OCH₂CH₂OMe SO₂CH₃ 6-117 CO₂Et CF₃ OCH₂(CO)NMe₂ SO2Me 6-118 CO₂Et CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-119 CO₂Et SMe SMe F 6-120 CO₂Et SMe SEt F 6-121 CO₂Et SO₂CH₃ F Cl 6-122 CO₂Et F S(O)Me CF₃ 6-123 CO₂Et F SMe CF₃ 6-124 CO₂Me NO₂ H SO₂Me 6-125 CO₂Me Cl H SO₂Me 6-126 CO₂Me SO₂Me H CF₃ 6-127 CO₂Me NO₂ H OMe 6-128 CO₂Me NO₂ H Br 6-129 CO₂Me NO₂ H CF₃ 6-130 CO₂Me NO₂ H NO₂ 6-131 CO₂Me NO₂ H Cl 6-132 CO₂Me NO₂ H Me 6-133 CO₂Me NO₂ H F 6-134 CO₂Me OMe H SO₂Me 6-135 CO₂Me CF₃ H NO₂ 6-136 CO₂Me CH₂SO₂Me H Br 6-137 CO₂Me Cl CH₂OCH₂CF₃ SO₂Me 6-138 CO₂Me Cl CH₂OCH₂CF₃ SMe 6-139 CO₂Me Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-140 CO₂Me Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-141 CO₂Me Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-142 CO₂Me Cl SMe Cl 6-143 CO₂Me Cl SMe SO₂Me 6-144 CO₂Me Cl Me SO₂Et 6-145 CO₂Me Cl O(CH₂)₂OMe Cl 6-146 CO₂Me Cl OCH₂-cyclopropyl Cl 6-147 CO₂Me Cl OMe Cl 6-148 CO₂Me Cl NHAc Cl 6-149 CO₂Me Cl OCH₂C(O)NMe₂ Cl 6-150 CO₂Me Cl Cl SO₂Me 6-151 CO₂Me Cl pyrazol-1-yl SO₂Me 6-152 CO₂Me Cl 4-methoxypyrazol-1-yl SO₂Me 6-153 CO₂Me Cl 1,2,3-triazol-1-yl SO₂Me 6-154 CO₂Me Cl 1,2,3-triazol-2-yl SO₂Me 6-155 CO₂Me Cl F SO₂Me 6-156 CO₂Me Me SO₂Me SO₂Me 6-157 CO₂Me Me SO₂Me CF₃ 6-158 CO₂Me Me NMe₂ SO₂Me 6-159 CO₂Me Me S(O)Me CF₃ 6-160 CO₂Me Me SMe CF₃ 6-161 CO₂Me Me SO₂CH₂CH₂OMe CF₃ 6-162 CO₂Me Me pyrazol-1-yl SO₂Me 6-163 CO₂Me Me 4-methoxypyrazol-1-yl SO₂Me 6-164 CO₂Me Me 1,2,3-triazol-1-yl SO₂Me 6-165 CO₂Me Me 1,2,3-triazol-2-yl SO₂Me 6-166 CO₂Me Me Cl SO₂Me 6-167 CO₂Me Me Me SO₂Me 6-168 CO₂Me Me Me SMe 6-169 CO₂Me Me SO₂Me Cl 6-170 CO₂Me Me NMe₂ SO₂Me 6-171 CO₂Me Me NH(CH₂)₂OMe SO₂Me 6-172 CO₂Me CF₃ F SO₂CH₃ 6-173 CO₂Me CF₃ SMe SO₂CH₃ 6-174 CO₂Me CF₃ SEt SO₂CH₃ 6-175 CO₂Me CF₃ S(O)Et SO₂CH₃ 6-176 CO₂Me CF₃ SO₂CH₃ SO₂CH₃ 6-177 CO₂Me CF₃ OCH₂CH₂OMe SO₂CH₃ 6-178 CO₂Me CF₃ OCH₂(CO)NMe₂ SO2Me 6-179 CO₂Me CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-180 CO₂Me SMe SMe F 6-181 CO₂Me SMe SEt F 6-182 CO₂Me SO₂CH₃ F Cl 6-183 CO₂Me F S(O)Me CF₃ 6-184 CO₂Me F SMe CF₃ 6-185 benzyl NO₂ H SO₂Me 6-186 benzyl Cl H SO₂Me 6-187 benzyl SO₂Me H CF₃ 6-188 benzyl NO₂ H OMe 6-189 benzyl NO₂ H Br 6-190 benzyl NO₂ H CF₃ 6-191 benzyl NO₂ H NO₂ 6-192 benzyl NO₂ H Cl 6-193 benzyl NO₂ H Me 6-194 benzyl NO₂ H F 6-195 benzyl OMe H SO₂Me 6-196 benzyl CF₃ H NO₂ 6-197 benzyl CH₂SO₂Me H Br 6-198 benzyl Cl CH₂OCH₂CF₃ SO₂Me 6-199 benzyl Cl CH₂OCH₂CF₃ SMe 6-200 benzyl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-201 benzyl Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-202 benzyl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-203 benzyl Cl SMe Cl 6-204 benzyl Cl SMe SO₂Me 6-205 benzyl Cl Me SO₂Et 6-206 benzyl Cl O(CH₂)₂OMe Cl 6-207 benzyl Cl OCH₂-cyclopropyl Cl 6-208 benzyl Cl OMe Cl 6-209 benzyl Cl NHAc Cl 6-210 benzyl Cl OCH₂C(O)NMe₂ Cl 6-211 benzyl Cl Cl SO₂Me 6-212 benzyl Cl pyrazol-1-yl SO₂Me 6-213 benzyl Cl 4-methoxypyrazol-1-yl SO₂Me 6-214 benzyl Cl 1,2,3-triazol-1-yl SO₂Me 6-215 benzyl Cl 1,2,3-triazol-2-yl SO₂Me 6-216 benzyl Cl F SO₂Me 6-217 benzyl Me SO₂Me SO₂Me 6-218 benzyl Me SO₂Me CF₃ 6-219 benzyl Me NMe₂ SO₂Me 6-220 benzyl Me S(O)Me CF₃ 6-221 benzyl Me SMe CF₃ 6-222 benzyl Me SO₂CH₂CH₂OMe CF₃ 6-223 benzyl Me pyrazol-1-yl SO₂Me 6-224 benzyl Me 4-methoxypyrazol-1-yl SO₂Me 6-225 benzyl Me 1,2,3-triazol-1-yl SO₂Me 6-226 benzyl Me 1,2,3-triazol-2-yl SO₂Me 6-227 benzyl Me Cl SO₂Me 6-228 benzyl Me Me SO₂Me 6-229 benzyl Me Me SMe 6-230 benzyl Me SO₂Me Cl 6-231 benzyl Me NMe₂ SO₂Me 6-232 benzyl Me NH(CH₂)₂OMe SO₂Me 6-233 benzyl CF₃ F SO₂CH₃ 6-234 benzyl CF₃ SMe SO₂CH₃ 6-235 benzyl CF₃ SEt SO₂CH₃ 6-236 benzyl CF₃ S(O)Et SO₂CH₃ 6-237 benzyl CF₃ SO₂CH₃ SO₂CH₃ 6-238 benzyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-239 benzyl CF₃ OCH₂(CO)NMe₂ SO2Me 6-240 benzyl CF₃ CH₂O-tetrahydrofuran-2-yl SO₂Et 6-241 benzyl SMe SMe F 6-242 benzyl SMe SEt F 6-243 benzyl SO₂CH₃ F Cl 6-244 benzyl F S(O)Me CF₃ 6-245 benzyl F SMe CF₃ 6-246 phenyl NO₂ H SO₂Me 6-247 phenyl Cl H SO₂Me 6-248 phenyl SO₂Me H CF₃ 6-249 phenyl NO₂ H OMe 6-250 phenyl NO₂ H Br 6-251 phenyl NO₂ H CF₃ 6-252 phenyl NO₂ H NO₂ 6-253 phenyl NO₂ H Cl 6-254 phenyl NO₂ H Me 6-255 phenyl NO₂ H F 6-256 phenyl OMe H SO₂Me 6-257 phenyl CF₃ H NO₂ 6-258 phenyl CH₂SO₂Me H Br 6-259 phenyl Cl CH₂OCH₂CF₃ SO₂Me 6-260 phenyl Cl CH₂OCH₂CF₃ SMe 6-261 phenyl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-262 phenyl Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-263 phenyl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-264 phenyl Cl SMe Cl 6-265 phenyl Cl SMe SO₂Me 6-266 phenyl Cl Me SO₂Et 6-267 phenyl Cl O(CH₂)₂OMe Cl 6-268 phenyl Cl OCH₂- Cl cyclopropyl 6-269 phenyl Cl OMe Cl 6-270 phenyl Cl NHAc Cl 6-271 phenyl Cl OCH₂C(O)NMe₂ Cl 6-272 phenyl Cl Cl SO₂Me 6-273 phenyl Cl pyrazol-1-yl SO₂Me 6-274 phenyl Cl 4-methoxypyrazol-1-yl SO₂Me 6-275 phenyl Cl 1,2,3-triazol-1-yl SO₂Me 6-276 phenyl Cl 1,2,3-triazol-2-yl SO₂Me 6-277 phenyl Cl F SO₂Me 6-278 phenyl Me SO₂Me SO₂Me 6-279 phenyl Me SO₂Me CF₃ 6-280 phenyl Me NMe₂ SO₂Me 6-281 phenyl Me S(O)Me CF₃ 6-282 phenyl Me SMe CF₃ 6-283 phenyl Me SO₂CH₂CH₂OMe CF₃ 6-284 phenyl Me pyrazol-1-yl SO₂Me 6-285 phenyl Me 4-methoxypyrazol-1-yl SO₂Me 6-286 phenyl Me 1,2,3-triazol-1-yl SO₂Me 6-287 phenyl Me 1,2,3-triazol-2-yl SO₂Me 6-288 phenyl Me Cl SO₂Me 6-289 phenyl Me Me SO₂Me 6-290 phenyl Me Me SMe 6-291 phenyl Me SO₂Me Cl 6-292 phenyl Me NMe₂ SO₂Me 6-293 phenyl Me NH(CH₂)₂OMe SO₂Me 6-294 phenyl CF₃ F SO₂CH₃ 6-295 phenyl CF₃ SMe SO₂CH₃ 6-296 phenyl CF₃ SEt SO₂CH₃ 6-297 phenyl CF₃ S(O)Et SO₂CH₃ 6-298 phenyl CF₃ SO₂CH₃ SO₂CH₃ 6-299 phenyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-300 phenyl CF₃ OCH₂(CO)NMe₂ SO2Me 6-301 phenyl CF₃ CH₂O-tetrahydrofuran-2-yl SO₂Et 6-302 phenyl SMe SMe F 6-303 phenyl SMe SEt F 6-304 phenyl SO₂CH₃ F Cl 6-305 phenyl F S(O)Me CF₃ 6-306 phenyl F SMe CF₃ 6-307 pyrazin-2-yl NO₂ H SO₂Me 6-308 pyrazin-2-yl Cl H SO₂Me 6-309 pyrazin-2-yl SO₂Me H CF₃ 6-310 pyrazin-2-yl NO₂ H OMe 6-311 pyrazin-2-yl NO₂ H Br 6-312 pyrazin-2-yl NO₂ H CF₃ 6-313 pyrazin-2-yl NO₂ H NO₂ 6-314 pyrazin-2-yl NO₂ H Cl 6-315 pyrazin-2-yl NO₂ H Me 6-316 pyrazin-2-yl NO₂ H F 6-317 pyrazin-2-yl OMe H SO₂Me 6-318 pyrazin-2-yl CF₃ H NO₂ 6-319 pyrazin-2-yl CH₂SO₂Me H Br 6-320 pyrazin-2-yl Cl CH₂OCH₂CF₃ SO₂Me 6-321 pyrazin-2-yl Cl CH₂OCH₂CF₃ SMe 6-322 pyrazin-2-yl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-323 pyrazin-2-yl Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-324 pyrazin-2-yl Cl CH₂OCH₂- SO₂Me tetrahydrofuran- 2-yl 6-325 pyrazin-2-yl Cl SMe Cl 6-326 pyrazin-2-yl Cl SMe SO₂Me 6-327 pyrazin-2-yl Cl Me SO₂Et 6-328 pyrazin-2-yl Cl O(CH₂)₂OMe Cl 6-329 pyrazin-2-yl Cl OCH₂-cyclopropyl Cl 6-330 pyrazin-2-yl Cl OMe Cl 6-331 pyrazin-2-yl Cl NHAc Cl 6-332 pyrazin-2-yl Cl OCH₂C(O)NMe₂ Cl 6-333 pyrazin-2-yl Cl Cl SO₂Me 6-334 pyrazin-2-yl Cl pyrazol-1-yl SO₂Me 6-335 pyrazin-2-yl Cl 4-methoxypyrazol-1-yl SO₂Me 6-336 pyrazin-2-yl Cl 1,2,3-triazol-1-yl SO₂Me 6-337 pyrazin-2-yl Cl 1,2,3-triazol-2-yl SO₂Me 6-338 pyrazin-2-yl Cl F SO₂Me 6-339 pyrazin-2-yl Me SO₂Me SO₂Me 6-340 pyrazin-2-yl Me SO₂Me CF₃ 6-341 pyrazin-2-yl Me NMe₂ SO₂Me 6-342 pyrazin-2-yl Me S(O)Me CF₃ 6-343 pyrazin-2-yl Me SMe CF₃ 6-344 pyrazin-2-yl Me SO₂CH₂CH₂OMe CF₃ 6-345 pyrazin-2-yl Me pyrazol-1-yl SO₂Me 6-346 pyrazin-2-yl Me 4-methoxypyrazol-1-yl SO₂Me 6-347 pyrazin-2-yl Me 1,2,3-triazol-1-yl SO₂Me 6-348 pyrazin-2-yl Me 1,2,3-triazol-2-yl SO₂Me 6-349 pyrazin-2-yl Me Cl SO₂Me 6-350 pyrazin-2-yl Me Me SO₂Me 6-351 pyrazin-2-yl Me Me SMe 6-352 pyrazin-2-yl Me SO₂Me Cl 6-353 pyrazin-2-yl Me NMe₂ SO₂Me 6-354 pyrazin-2-yl Me NH(CH₂)₂OMe SO₂Me 6-355 pyrazin-2-yl CF₃ F SO₂CH₃ 6-356 pyrazin-2-yl CF₃ SMe SO₂CH₃ 6-357 pyrazin-2-yl CF₃ SEt SO₂CH₃ 6-358 pyrazin-2-yl CF₃ S(O)Et SO₂CH₃ 6-359 pyrazin-2-yl CF₃ SO₂CH₃ SO₂CH₃ 6-360 pyrazin-2-yl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-361 pyrazin-2-yl CF₃ OCH₂(CO)NMe₂ SO2Me 6-362 pyrazin-2-yl CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-363 pyrazin-2-yl SMe SMe F 6-364 pyrazin-2-yl SMe SEt F 6-365 pyrazin-2-yl SO₂CH₃ F Cl 6-366 pyrazin-2-yl F S(O)Me CF₃ 6-367 pyrazin-2-yl F SMe CF₃ 6-368 4-OMe—Ph NO₂ H SO₂Me 6-369 4-OMe—Ph Cl H SO₂Me 6-370 4-OMe—Ph SO₂Me H CF₃ 6-371 4-OMe—Ph NO₂ H OMe 6-372 4-OMe—Ph NO₂ H Br 6-373 4-OMe—Ph NO₂ H CF₃ 6-374 4-OMe—Ph NO₂ H NO₂ 6-375 4-OMe—Ph NO₂ H Cl 6-376 4-OMe—Ph NO₂ H Me 6-377 4-OMe—Ph NO₂ H F 6-378 4-OMe—Ph OMe H SO₂Me 6-379 4-OMe—Ph CF₃ H NO₂ 6-380 4-OMe—Ph CH₂SO₂Me H Br 6-381 4-OMe—Ph Cl CH₂OCH₂CF₃ SO₂Me 6-382 4-OMe—Ph Cl CH₂OCH₂CF₃ SMe 6-383 4-OMe—Ph Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-384 4-OMe—Ph Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-385 4-OMe—Ph Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-386 4-OMe—Ph Cl SMe Cl 6-387 4-OMe—Ph Cl SMe SO₂Me 6-388 4-OMe—Ph Cl Me SO₂Et 6-389 4-OMe—Ph Cl O(CH₂)₂OMe Cl 6-390 4-OMe—Ph Cl OCH₂- Cl cyclopropyl 6-391 4-OMe—Ph Cl OMe Cl 6-392 4-OMe—Ph Cl NHAc Cl 6-393 4-OMe—Ph Cl OCH₂C(O)NMe₂ Cl 6-394 4-OMe—Ph Cl Cl SO₂Me 6-395 4-OMe—Ph Cl pyrazol-1-yl SO₂Me 6-396 4-OMe—Ph Cl 4-methoxypyrazol-1-yl SO₂Me 6-397 4-OMe—Ph Cl 1,2,3-triazol-1-yl SO₂Me 6-398 4-OMe—Ph Cl 1,2,3-triazol-2-yl SO₂Me 6-399 4-OMe—Ph Cl F SO₂Me 6-400 4-OMe—Ph Me SO₂Me SO₂Me 6-401 4-OMe—Ph Me SO₂Me CF₃ 6-402 4-OMe—Ph Me NMe₂ SO₂Me 6-403 4-OMe—Ph Me S(O)Me CF₃ 6-404 4-OMe—Ph Me SMe CF₃ 6-405 4-OMe—Ph Me SO₂CH₂CH₂OMe CF₃ 6-406 4-OMe—Ph Me pyrazol-1-yl SO₂Me 6-407 4-OMe—Ph Me 4-methoxypyrazol-1-yl SO₂Me 6-408 4-OMe—Ph Me 1,2,3-triazol-1-yl SO₂Me 6-409 4-OMe—Ph Me 1,2,3-triazol-2-yl SO₂Me 6-410 4-OMe—Ph Me Cl SO₂Me 6-411 4-OMe—Ph Me Me SO₂Me 6-412 4-OMe—Ph Me Me SMe 6-413 4-OMe—Ph Me SO₂Me Cl 6-414 4-OMe—Ph Me NMe₂ SO₂Me 6-415 4-OMe—Ph Me NH(CH₂)₂OMe SO₂Me 6-416 4-OMe—Ph CF₃ F SO₂CH₃ 6-417 4-OMe—Ph CF₃ SMe SO₂CH₃ 6-418 4-OMe—Ph CF₃ SEt SO₂CH₃ 6-419 4-OMe—Ph CF₃ S(O)Et SO₂CH₃ 6-420 4-OMe—Ph CF₃ SO₂CH₃ SO₂CH₃ 6-421 4-OMe—Ph CF₃ OCH₂CH₂OMe SO₂CH₃ 6-422 4-OMe—Ph CF₃ OCH₂(CO)NMe₂ SO2Me 6-423 4-OMe—Ph CF₃ CH₂O-tetrahydrofuran-2-yl SO₂Et 6-424 4-OMe—Ph SMe SMe F 6-425 4-OMe—Ph SMe SEt F 6-426 4-OMe—Ph SO₂CH₃ F Cl 6-427 4-OMe—Ph F S(O)Me CF₃ 6-428 4-OMe—Ph F SMe CF₃ 6-429 4-Cl—Ph NO₂ H SO₂Me 6-430 4-Cl—Ph Cl H SO₂Me 6-431 4-Cl—Ph SO₂Me H CF₃ 6-432 4-Cl—Ph NO₂ H OMe 6-433 4-Cl—Ph NO₂ H Br 6-434 4-Cl—Ph NO₂ H CF₃ 6-435 4-Cl—Ph NO₂ H NO₂ 6-436 4-Cl—Ph NO₂ H Cl 6-437 4-Cl—Ph NO₂ H Me 6-438 4-Cl—Ph NO₂ H F 6-439 4-Cl—Ph OMe H SO₂Me 6-440 4-Cl—Ph CF₃ H NO₂ 6-441 4-Cl—Ph CH₂SO₂Me H Br 6-442 4-Cl—Ph Cl CH₂OCH₂CF₃ SO₂Me 6-443 4-Cl—Ph Cl CH₂OCH₂CF₃ SMe 6-444 4-Cl—Ph Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-445 4-Cl—Ph Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-446 4-Cl—Ph Cl CH₂OCH₂-tetrahydrofuran- SO₂Me 2-yl 6-447 4-Cl—Ph Cl SMe Cl 6-448 4-Cl—Ph Cl SMe SO₂Me 6-449 4-Cl—Ph Cl Me SO₂Et 6-450 4-Cl—Ph Cl O(CH₂)₂OMe Cl 6-451 4-Cl—Ph Cl OCH₂- Cl cyclopropyl 6-452 4-Cl—Ph Cl OMe Cl 6-453 4-Cl—Ph Cl NHAc Cl 6-454 4-Cl—Ph Cl OCH₂C(O)NMe₂ Cl 6-455 4-Cl—Ph Cl Cl SO₂Me 6-456 4-Cl—Ph Cl pyrazol-1-yl SO₂Me 6-457 4-Cl—Ph Cl 4- SO₂Me methoxypyrazol-1-yl 6-458 4-Cl—Ph Cl 1,2,3-triazol-1-yl SO₂Me 6-459 4-Cl—Ph Cl 1,2,3-triazol-2-yl SO₂Me 6-460 4-Cl—Ph Cl F SO₂Me 6-461 4-Cl—Ph Me SO₂Me SO₂Me 6-462 4-Cl—Ph Me SO₂Me CF₃ 6-463 4-Cl—Ph Me NMe₂ SO₂Me 6-464 4-Cl—Ph Me S(O)Me CF₃ 6-465 4-Cl—Ph Me SMe CF₃ 6-466 4-Cl—Ph Me SO₂CH₂CH₂OMe CF₃ 6-467 4-Cl—Ph Me pyrazol-1-yl SO₂Me 6-468 4-Cl—Ph Me 4- SO₂Me methoxypyrazol-1-yl 6-469 4-Cl—Ph Me 1,2,3-triazol-1-yl SO₂Me 6-470 4-Cl—Ph Me 1,2,3-triazol-2-yl SO₂Me 6-471 4-Cl—Ph Me Cl SO₂Me 6-472 4-Cl—Ph Me Me SO₂Me 6-473 4-Cl—Ph Me Me SMe 6-474 4-Cl—Ph Me SO₂Me Cl 6-475 4-Cl—Ph Me NMe₂ SO₂Me 6-476 4-Cl—Ph Me NH(CH₂)₂OMe SO₂Me 6-477 4-Cl—Ph CF₃ F SO₂CH₃ 6-478 4-Cl—Ph CF₃ SMe SO₂CH₃ 6-479 4-Cl—Ph CF₃ SEt SO₂CH₃ 6-480 4-Cl—Ph CF₃ S(O)Et SO₂CH₃ 6-481 4-Cl—Ph CF₃ SO₂CH₃ SO₂CH₃ 6-482 4-Cl—Ph CF₃ OCH₂CH₂OMe SO₂CH₃ 6-483 4-Cl—Ph CF₃ OCH₂(CO)NMe₂ SO2Me 6-484 4-Cl—Ph CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-485 4-Cl—Ph SMe SMe F 6-486 4-Cl—Ph SMe SEt F 6-487 4-Cl—Ph SO₂CH₃ F Cl 6-488 4-Cl—Ph F S(O)Me CF₃ 6-489 4-Cl—Ph F SMe CF₃ 6-490 tert-butyl NO₂ H SO₂Me 6-491 tert-butyl Cl H SO₂Me 6-492 tert-butyl SO₂Me H CF₃ 6-493 tert-butyl NO₂ H OMe 6-494 tert-butyl NO₂ H Br 6-495 tert-butyl NO₂ H CF₃ 6-496 tert-butyl NO₂ H NO₂ 6-497 tert-butyl NO₂ H Cl 6-498 tert-butyl NO₂ H Me 6-499 tert-butyl NO₂ H F 6-500 tert-butyl OMe H SO₂Me 6-501 tert-butyl CF₃ H NO₂ 6-502 tert-butyl CH₂SO₂Me H Br 6-503 tert-butyl Cl CH₂OCH₂CF₃ SO₂Me 6-504 tert-butyl Cl CH₂OCH₂CF₃ SMe 6-505 tert-butyl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-506 tert-butyl Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-507 tert-butyl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-508 tert-butyl Cl SMe Cl 6-509 tert-butyl Cl SMe SO₂Me 6-510 tert-butyl Cl Me SO₂Et 6-511 tert-butyl Cl O(CH₂)₂OMe Cl 6-512 tert-butyl Cl OCH₂-cyclopropyl Cl 6-513 tert-butyl Cl OMe Cl 6-514 tert-butyl Cl NHAc Cl 6-515 tert-butyl Cl OCH₂C(O)NMe₂ Cl 6-516 tert-butyl Cl Cl SO₂Me 6-517 tert-butyl Cl pyrazol-1 -yl SO₂Me 6-518 tert-butyl Cl 4-methoxypyrazol-1-yl SO₂Me 6-519 tert-butyl Cl 1,2,3-triazol-1-yl SO₂Me 6-520 tert-butyl Cl 1,2,3-triazol-2-yl SO₂Me 6-521 tert-butyl Cl F SO₂Me 6-522 tert-butyl Me SO₂Me SO₂Me 6-523 tert-butyl Me SO₂Me CF₃ 6-524 tert-butyl Me NMe₂ SO₂Me 6-525 tert-butyl Me S(O)Me CF₃ 6-526 tert-butyl Me SMe CF₃ 6-527 tert-butyl Me SO₂CH₂CH₂OMe CF₃ 6-528 tert-butyl Me pyrazol-1-yl SO₂Me 6-529 tert-butyl Me 4-methoxypyrazol-1-yl SO₂Me 6-530 tert-butyl Me 1,2,3-triazol-1-yl SO₂Me 6-531 tert-butyl Me 1,2,3-triazol-2-yl SO₂Me 6-532 tert-butyl Me Cl SO₂Me 6-533 tert-butyl Me Me SO₂Me 6-534 tert-butyl Me Me SMe 6-535 tert-butyl Me SO₂Me Cl 6-536 tert-butyl Me NMe₂ SO₂Me 6-537 tert-butyl Me NH(CH₂)₂OMe SO₂Me 6-538 tert-butyl CF₃ F SO₂CH₃ 6-539 tert-butyl CF₃ SMe SO₂CH₃ 6-540 tert-butyl CF₃ SEt SO₂CH₃ 6-541 tert-butyl CF₃ S(O)Et SO₂CH₃ 6-542 tert-butyl CF₃ SO₂CH₃ SO₂CH₃ 6-543 tert-butyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-544 tert-butyl CF₃ OCH₂(CO)NMe₂ SO2Me 6-545 tert-butyl CF₃ CH₂O-tetrahydrofuran-2-yl SO₂Et 6-546 tert-butyl SMe SMe F 6-547 tert-butyl SMe SEt F 6-548 tert-butyl SO₂CH₃ F Cl 6-549 tert-butyl F S(O)Me CF₃ 6-550 tert-butyl F SMe CF₃ 6-551 furan-2-yl NO₂ H SO₂Me 6-552 furan-2-yl Cl H SO₂Me 6-553 furan-2-yl SO₂Me H CF₃ 6-554 furan-2-yl NO₂ H OMe 6-555 furan-2-yl NO₂ H Br 6-556 furan-2-yl NO₂ H CF₃ 6-557 furan-2-yl NO₂ H NO₂ 6-558 furan-2-yl NO₂ H Cl 6-559 furan-2-yl NO₂ H Me 6-560 furan-2-yl NO₂ H F 6-561 furan-2-yl OMe H SO₂Me 6-562 furan-2-yl CF₃ H NO₂ 6-563 furan-2-yl CH₂SO₂Me H Br 6-564 furan-2-yl Cl CH₂OCH₂CF₃ SO₂Me 6-565 furan-2-yl Cl CH₂OCH₂CF₃ SMe 6-566 furan-2-yl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-567 furan-2-yl Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-568 furan-2-yl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-569 furan-2-yl Cl SMe Cl 6-570 furan-2-yl Cl SMe SO₂Me 6-571 furan-2-yl Cl Me SO₂Et 6-572 furan-2-yl Cl O(CH₂)₂OMe Cl 6-573 furan-2-yl Cl OCH₂-cyclopropyl Cl 6-574 furan-2-yl Cl OMe Cl 6-575 furan-2-yl Cl NHAc Cl 6-576 furan-2-yl Cl OCH₂C(O)NMe₂ Cl 6-577 furan-2-yl Cl Cl SO₂Me 6-578 furan-2-yl Cl pyrazol-l-yl SO₂Me 6-579 furan-2-yl Cl 4-methoxypyrazol-1-yl SO₂Me 6-580 furan-2-yl Cl 1,2,3-triazol-1-yl SO₂Me 6-581 furan-2-yl Cl 1,2,3-triazol-2-yl SO₂Me 6-582 furan-2-yl Cl F SO₂Me 6-583 furan-2-yl Me SO₂Me SO₂Me 6-584 furan-2-yl Me SO₂Me CF₃ 6-585 furan-2-yl Me NMe₂ SO₂Me 6-586 furan-2-yl Me S(O)Me CF₃ 6-587 furan-2-yl Me SMe CF₃ 6-588 furan-2-yl Me SO₂CH₂CH₂OMe CF₃ 6-589 furan-2-yl Me pyrazol-1-yl SO₂Me 6-590 furan-2-yl Me 4-methoxypyrazol-1-yl SO₂Me 6-591 furan-2-yl Me 1,2,3-triazol-1-yl SO₂Me 6-592 furan-2-yl Me 1,2,3-triazol-2-yl SO₂Me 6-593 furan-2-yl Me Cl SO₂Me 6-594 furan-2-yl Me Me SO₂Me 6-595 furan-2-yl Me Me SMe 6-596 furan-2-yl Me SO₂Me Cl 6-597 furan-2-yl Me NMe₂ SO₂Me 6-598 furan-2-yl Me NH(CH₂)₂OMe SO₂Me 6-599 furan-2-yl CF₃ F SO₂CH₃ 6-600 furan-2-yl CF₃ SMe SO₂CH₃ 6-601 furan-2-yl CF₃ SEt SO₂CH₃ 6-602 furan-2-yl CF₃ S(O)Et SO₂CH₃ 6-603 furan-2-yl CF₃ SO₂CH₃ SO₂CH₃ 6-604 furan-2-yl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-605 furan-2-yl CF₃ OCH₂(CO)NMe₂ SO2Me 6-606 furan-2-yl CF₃ CH₂O-tetrahydrofuran-2-yl SO₂Et 6-607 furan-2-yl SMe SMe F 6-608 furan-2-yl SMe SEt F 6-609 furan-2-yl SO₂CH₃ F Cl 6-610 furan-2-yl F S(O)Me CF₃ 6-611 furan-2-yl F SMe CF₃ 6-612 isopropyl NO₂ H SO₂Me 6-613 isopropyl Cl H SO₂Me 6-614 isopropyl SO₂Me H CF₃ 6-615 isopropyl NO₂ H OMe 6-616 isopropyl NO₂ H Br 6-617 isopropyl NO₂ H CF₃ 6-618 isopropyl NO₂ H NO₂ 6-619 isopropyl NO₂ H Cl 6-620 isopropyl NO₂ H Me 6-621 isopropyl NO₂ H F 6-622 isopropyl OMe H SO₂Me 6-623 isopropyl CF₃ H NO₂ 6-624 isopropyl CH₂SO₂Me H Br 6-625 isopropyl Cl CH₂OCH₂CF₃ SO₂Me 6-626 isopropyl Cl CH₂OCH₂CF₃ SMe 6-627 isopropyl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-628 isopropyl Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-629 isopropyl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-630 isopropyl Cl SMe Cl 6-631 isopropyl Cl SMe SO₂Me 6-632 isopropyl Cl Me SO₂Et 6-633 isopropyl Cl O(CH₂)₂OMe Cl 6-634 isopropyl Cl OCH₂-cyclopropyl Cl 6-635 isopropyl Cl OMe Cl 6-636 isopropyl Cl NHAc Cl 6-637 isopropyl Cl OCH₂C(O)NMe₂ Cl 6-638 isopropyl Cl Cl SO₂Me 6-639 isopropyl Cl pyrazol-1-yl SO₂Me 6-640 isopropyl Cl 4-methoxypyrazol-1-yl SO₂Me 6-641 isopropyl Cl 1,2,3-triazol-1-yl SO₂Me 6-642 isopropyl Cl 1,2,3-triazol-2-yl SO₂Me 6-643 isopropyl Cl F SO₂Me 6-644 isopropyl Me SO₂Me SO₂Me 6-645 isopropyl Me SO₂Me CF₃ 6-646 isopropyl Me NMe₂ SO₂Me 6-647 isopropyl Me S(O)Me CF₃ 6-648 isopropyl Me SMe CF₃ 6-649 isopropyl Me SO₂CH₂CH₂OMe CF₃ 6-650 isopropyl Me pyrazol-1-yl SO₂Me 6-651 isopropyl Me 4-methoxypyrazol-1-yl SO₂Me 6-652 isopropyl Me 1,2,3-triazol-1-yl SO₂Me 6-653 isopropyl Me 1,2,3-triazol-2-yl SO₂Me 6-654 isopropyl Me Cl SO₂Me 6-655 isopropyl Me Me SO₂Me 6-656 isopropyl Me F Cl 6-657 isopropyl Me SO₂Me Cl 6-658 isopropyl Me NMe₂ SO₂Me 6-659 isopropyl Me NH(CH₂)₂OMe SO₂Me 6-660 isopropyl CF₃ F SO₂CH₃ 6-661 isopropyl CF₃ SMe SO₂CH₃ 6-662 isopropyl CF₃ SEt SO₂CH₃ 6-663 isopropyl CF₃ S(O)Et SO₂CH₃ 6-664 isopropyl CF₃ SO₂CH₃ SO₂CH₃ 6-665 isopropyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-666 isopropyl CF₃ OCH₂(CO)NMe₂ SO2Me 6-667 isopropyl CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-668 isopropyl SMe SMe F 6-669 isopropyl SMe SEt F 6-670 isopropyl SO₂CH₃ F Cl 6-671 isopropyl F S(O)Me CF₃ 6-672 isopropyl F SMe CF₃ 6-673 CH₂CH₂OMe NO₂ H SO₂Me 6-674 CH₂CH₂OMe Cl H SO₂Me 6-675 CH₂CH₂OMe SO₂Me H CF₃ 6-676 CH₂CH₂OMe NO₂ H OMe 6-677 CH₂CH₂OMe NO₂ H Br 6-678 CH₂CH₂OMe NO₂ H CF₃ 6-679 CH₂CH₂OMe NO₂ H NO₂ 6-680 CH₂CH₂OMe NO₂ H Cl 6-681 CH₂CH₂OMe NO₂ H Me 6-682 CH₂CH₂OMe NO₂ H F 6-683 CH₂CH₂OMe OMe H SO₂Me 6-684 CH₂CH₂OMe CF₃ H NO₂ 6-685 CH₂CH₂OMe CH₂SO₂Me H Br 6-686 CH₂CH₂OMe Cl CH₂OCH₂CF₃ SO₂Me 6-687 CH₂CH₂OMe Cl CH₂OCH₂CF₃ SMe 6-688 CH₂CH₂OMe Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-689 CH₂CH₂OMe Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-690 CH₂CH₂OMe Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-691 CH₂CH₂OMe Cl SMe Cl 6-692 CH₂CH₂OMe Cl SMe SO₂Me 6-693 CH₂CH₂OMe Cl Me SO₂Et 6-694 CH₂CH₂OMe Cl O(CH₂)₂OMe Cl 6-695 CH₂CH₂OMe Cl OCH₂-cyclopropyl Cl 6-696 CH₂CH₂OMe Cl OMe Cl 6-697 CH₂CH₂OMe Cl NHAc Cl 6-698 CH₂CH₂OMe Cl OCH₂C(O)NMe₂ Cl 6-699 CH₂CH₂OMe Cl Cl SO₂Me 6-700 CH₂CH₂OMe Cl pyrazol-1-yl SO₂Me 6-701 CH₂CH₂OMe Cl 4-methoxypyrazol-1-yl SO₂Me 6-702 CH₂CH₂OMe Cl 1,2,3-triazol-1-yl SO₂Me 6-703 CH₂CH₂OMe Cl 1,2,3-triazol-2-yl SO₂Me 6-704 CH₂CH₂OMe Cl F SO₂Me 6-705 CH₂CH₂OMe Me SO₂Me SO₂Me 6-706 CH₂CH₂OMe Me SO₂Me CF₃ 6-707 CH₂CH₂OMe Me NMe₂ SO₂Me 6-708 CH₂CH₂OMe Me S(O)Me CF₃ 6-709 CH₂CH₂OMe Me SMe CF₃ 6-710 CH₂CH₂OMe Me SO₂CH₂CH₂OMe CF₃ 6-711 CH₂CH₂OMe Me pyrazol-1-yl SO₂Me 6-712 CH₂CH₂OMe Me 4-methoxypyrazol-1-yl SO₂Me 6-713 CH₂CH₂OMe Me 1,2,3-triazol-1-yl SO₂Me 6-714 CH₂CH₂OMe Me 1,2,3-triazol-2-yl SO₂Me 6-715 CH₂CH₂OMe Me Cl SO₂Me 6-716 CH₂CH₂OMe Me Me SO₂Me 6-717 CH₂CH₂OMe Me Me SMe 6-718 CH₂CH₂OMe Me SO₂Me Cl 6-719 CH₂CH₂OMe Me NMe₂ SO₂Me 6-720 CH₂CH₂OMe Me NH(CH₂)₂OMe SO₂Me 6-721 CH₂CH₂OMe CF₃ F SO₂CH₃ 6-722 CH₂CH₂OMe CF₃ SMe SO₂CH₃ 6-723 CH₂CH₂OMe CF₃ SEt SO₂CH₃ 6-724 CH₂CH₂OMe CF₃ S(O)Et SO₂CH₃ 6-725 CH₂CH₂OMe CF₃ SO₂CH₃ SO₂CH₃ 6-726 CH₂CH₂OMe CF₃ OCH₂CH₂OMe SO₂CH₃ 6-727 CH₂CH₂OMe CF₃ OCH₂(CO)NMe₂ SO2Me 6-728 CH₂CH₂OMe CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-729 CH₂CH₂OMe SMe SMe F 6-730 CH₂CH₂OMe SMe SEt F 6-731 CH₂CH₂OMe SO₂CH₃ F Cl 6-732 CH₂CH₂OMe F S(O)Me CF₃ 6-733 CH₂CH₂OMe F SMe CF₃ 6-734 CH₂CF₃ NO₂ H SO₂Me 6-735 CH₂CF₃ Cl H SO₂Me 6-736 CH₂CF₃ SO₂Me H CF₃ 6-737 CH₂CF₃ NO₂ H OMe 6-738 CH₂CF₃ NO₂ H Br 6-739 CH₂CF₃ NO₂ H CF₃ 6-740 CH₂CF₃ NO₂ H NO₂ 6-741 CH₂CF₃ NO₂ H Cl 6-742 CH₂CF₃ NO₂ H Me 6-743 CH₂CF₃ NO₂ H F 6-744 CH₂CF₃ OMe H SO₂Me 6-745 CH₂CF₃ CF₃ H NO₂ 6-746 CH₂CF₃ CH₂SO₂Me H Br 6-747 CH₂CF₃ Cl CH₂OCH₂CF₃ SO₂Me 6-748 CH₂CF₃ Cl CH₂OCH₂CF₃ SMe 6-749 CH₂CF₃ Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-750 CH₂CF₃ Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-751 CH₂CF₃ Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-752 CH₂CF₃ Cl SMe Cl 6-753 CH₂CF₃ Cl SMe SO₂Me 6-754 CH₂CF₃ Cl Me SO₂Et 6-755 CH₂CF₃ Cl O(CH₂)₂OMe Cl 6-756 CH₂CF₃ Cl OCH₂-cyclopropyl Cl 6-757 CH₂CF₃ Cl OMe Cl 6-758 CH₂CF₃ Cl NHAc Cl 6-759 CH₂CF₃ Cl OCH₂C(O)NMe₂ Cl 6-760 CH₂CF₃ Cl Cl SO₂Me 6-761 CH₂CF₃ Cl pyrazol-1-yl SO₂Me 6-762 CH₂CF₃ Cl 4-methoxypyrazol-1-yl SO₂Me 6-763 CH₂CF₃ Cl 1,2,3-triazol-1-yl SO₂Me 6-764 CH₂CF₃ Cl 1,2,3-triazol-2-yl SO₂Me 6-765 CH₂CF₃ Cl F SO₂Me 6-766 CH₂CF₃ Me SO₂Me SO₂Me 6-767 CH₂CF₃ Me SO₂Me CF₃ 6-768 CH₂CF₃ Me NMe₂ SO₂Me 6-769 CH₂CF₃ Me S(O)Me CF₃ 6-770 CH₂CF₃ Me SMe CF₃ 6-771 CH₂CF₃ Me SO₂CH₂CH₂OMe CF₃ 6-772 CH₂CF₃ Me pyrazol-1-yl SO₂Me 6-773 CH₂CF₃ Me 4-methoxypyrazol-1-yl SO₂Me 6-774 CH₂CF₃ Me 1,2,3-triazol-1-yl SO₂Me 6-775 CH₂CF₃ Me 1,2,3-triazol-2-yl SO₂Me 6-776 CH₂CF₃ Me Cl SO₂Me 6-777 CH₂CF₃ Me Me SO₂Me 6-778 CH₂CF₃ Me Me SMe 6-779 CH₂CF₃ Me SO₂Me Cl 6-780 CH₂CF₃ Me NMe₂ SO₂Me 6-781 CH₂CF₃ Me NH(CH₂)₂OMe SO₂Me 6-782 CH₂CF₃ CF₃ F SO₂CH₃ 6-783 CH₂CF₃ CF₃ SMe SO₂CH₃ 6-784 CH₂CF₃ CF₃ SEt SO₂CH₃ 6-785 CH₂CF₃ CF₃ S(O)Et SO₂CH₃ 6-786 CH₂CF₃ CF₃ SO₂CH₃ SO₂CH₃ 6-787 CH₂CF₃ CF₃ OCH₂CH₂OMe SO₂CH₃ 6-788 CH₂CF₃ CF₃ OCH₂(CO)NMe₂ SO2Me 6-789 CH₂CF₃ CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-790 CH₂CF₃ SMe SMe F 6-791 CH₂CF₃ SMe SEt F 6-792 CH₂CF₃ SO₂CH₃ F Cl 6-793 CH₂CF₃ F S(O)Me CF₃ 6-794 CH₂CF₃ F SMe CF₃ 6-795 tetrahydrofuran-2-yl NO₂ H SO₂Me 6-796 tetrahydrofuran-2-yl Cl H SO₂Me 6-797 tetrahydrofuran-2-yl SO₂Me H CF₃ 6-798 tetrahydrofuran-2-yl NO₂ H OMe 6-799 tetrahydrofuran-2-yl NO₂ H Br 6-800 tetrahydrofuran-2-yl NO₂ H CF₃ 6-801 tetrahydrofuran-2-yl NO₂ H NO₂ 6-802 tetrahydrofuran-2-yl NO₂ H Cl 6-803 tetrahydrofuran-2-yl NO₂ H Me 6-804 tetrahydrofuran-2-yl NO₂ H F 6-805 tetrahydrofuran-2-yl OMe H SO₂Me 6-806 tetrahydrofuran-2-yl CF₃ H NO₂ 6-807 tetrahydrofuran-2-yl CH₂SO₂Me H Br 6-808 tetrahydrofuran-2-yl Cl CH₂OCH₂CF₃ SO₂Me 6-809 tetrahydrofuran-2-yl Cl CH₂OCH₂CF₃ SMe 6-810 tetrahydrofuran-2-yl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-811 tetrahydrofuran-2-yl Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-812 tetrahydrofuran-2-yl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-813 tetrahydrofuran-2-yl Cl SMe Cl 6-814 tetrahydrofuran-2-yl Cl SMe SO₂Me 6-815 tetrahydrofuran-2-yl Cl Me SO₂Et 6-816 tetrahydrofuran-2-yl Cl O(CH₂)₂OMe Cl 6-817 tetrahydrofuran-2-yl Cl OCH₂-cyclopropyl Cl 6-818 tetrahydrofuran-2-yl Cl OMe Cl 6-819 tetrahydrofuran-2-yl Cl NHAc Cl 6-820 tetrahydrofuran-2-yl Cl OCH₂C(O)NMe₂ Cl 6-821 tetrahydrofuran-2-yl Cl Cl SO₂Me 6-822 tetrahydrofuran-2-yl Cl pyrazol-1-yl SO₂Me 6-823 tetrahydrofuran-2-yl Cl 4-methoxypyrazol-1-yl SO₂Me 6-824 tetrahydrofuran-2-yl Cl 1,2,3-triazol-1-yl SO₂Me 6-825 tetrahydrofuran-2-yl Cl 1,2,3-triazol-2-yl SO₂Me 6-826 tetrahydrofuran-2-yl Cl F SO₂Me 6-827 tetrahydrofuran-2-yl Me SO₂Me SO₂Me 6-828 tetrahydrofuran-2-yl Me SO₂Me CF₃ 6-829 tetrahydrofuran-2-yl Me NMe₂ SO₂Me 6-830 tetrahydrofuran-2-yl Me S(O)Me CF₃ 6-831 tetrahydrofuran-2-yl Me SMe CF₃ 6-832 tetrahydrofuran-2-yl Me SO₂CH₂CH₂OMe CF₃ 6-833 tetrahydrofuran-2-yl Me pyrazol-1-yl SO₂Me 6-834 tetrahydrofuran-2-yl Me 4-methoxypyrazol-1-yl SO₂Me 6-835 tetrahydrofuran-2-yl Me 1,2,3-triazol-1-yl SO₂Me 6-836 tetrahydrofuran-2-yl Me 1,2,3-triazol-2-yl SO₂Me 6-837 tetrahydrofuran-2-yl Me Cl SO₂Me 6-838 tetrahydrofuran-2-yl Me Me SO₂Me 6-839 tetrahydrofuran-2-yl Me Me SMe 6-840 tetrahydrofuran-2-yl Me SO₂Me Cl 6-841 tetrahydrofuran-2-yl Me NMe₂ SO₂Me 6-842 tetrahydrofuran-2-yl Me NH(CH₂)₂OMe SO₂Me 6-843 tetrahydrofuran-2-yl CF₃ F SO₂CH₃ 6-844 tetrahydrofuran-2-yl CF₃ SMe SO₂CH₃ 6-845 tetrahydrofuran-2-yl CF₃ SEt SO₂CH₃ 6-846 tetrahydrofuran-2-yl CF₃ S(O)Et SO₂CH₃ 6-847 tetrahydrofuran-2-yl CF₃ SO₂CH₃ SO₂CH₃ 6-848 tetrahydrofuran-2-yl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-849 tetrahydrofuran-2-yl CF₃ OCH₂(CO)NMe₂ SO2Me 6-850 tetrahydrofuran-2-yl CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-851 tetrahydrofuran-2-yl SMe SMe F 6-852 tetrahydrofuran-2-yl SMe SEt F 6-853 tetrahydrofuran-2-yl SO₂CH₃ F Cl 6-854 tetrahydrofuran-2-yl F S(O)Me CF₃ 6-855 tetrahydrofuran-2-yl F SMe CF₃ 6-856 n-Pr NO₂ H SO₂Me 6-857 n-Pr Cl H SO₂Me 6-858 n-Pr SO₂Me H CF₃ 6-859 n-Pr NO₂ H OMe 6-860 n-Pr NO₂ H Br 6-861 n-Pr NO₂ H Cl 6-862 n-Pr NO₂ H CF₃ 6-863 n-Pr NO₂ H NO₂ 6-864 n-Pr NO₂ H Me 6-865 n-Pr NO₂ H F 6-866 n-Pr OMe H SO₂Me 6-867 n-Pr CF₃ H NO₂ 6-868 n-Pr CH₂SO₂Me H Br 6-869 n-Pr Cl CH₂OCH₂CF₃ SO₂Me 6-870 n-Pr Cl CH₂OCH₂CF₃ SMe 6-871 n-Pr Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-872 n-Pr Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-873 n-Pr Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-874 n-Pr Cl SMe Cl 6-875 n-Pr Cl SMe SO₂Me 6-876 n-Pr Cl Me SO₂Et 6-877 n-Pr Cl O(CH₂)₂OMe Cl 6-878 n-Pr Cl OCH₂-cyclopropyl Cl 6-879 n-Pr Cl OMe Cl 6-880 n-Pr Cl NHAc Cl 6-881 n-Pr Cl OCH₂C(O)NMe₂ Cl 6-882 n-Pr Cl Cl SO₂Me 6-883 n-Pr Cl pyrazol-1-yl SO₂Me 6-884 n-Pr Cl 4-methoxypyrazol-1-yl SO₂Me 6-885 n-Pr Cl 1,2,3-triazol-1-yl SO₂Me 6-886 n-Pr Cl 1,2,3-triazol-2-yl SO₂Me 6-887 n-Pr Cl F SO₂Me 6-888 n-Pr Me SO₂Me SO₂Me 6-889 n-Pr Me SO₂Me CF₃ 6-890 n-Pr Me NMe₂ SO₂Me 6-891 n-Pr Me S(O)Me CF₃ 6-892 n-Pr Me SMe CF₃ 6-893 n-Pr Me SO₂CH₂CH₂OMe CF₃ 6-894 n-Pr Me pyrazol-1-yl SO₂Me 6-895 n-Pr Me 4-methoxypyrazol-1-yl SO₂Me 6-896 n-Pr Me 1,2,3-triazol-1-yl SO₂Me 6-897 n-Pr Me 1,2,3-triazol-2-yl SO₂Me 6-898 n-Pr Me Cl SO₂Me 6-899 n-Pr Me Me SO₂Me 6-900 n-Pr Me Me SMe 6-901 n-Pr Me SO₂Me Cl 6-902 n-Pr Me NMe₂ SO₂Me 6-903 n-Pr Me NH(CH₂)₂OMe SO₂Me 6-904 n-Pr CF₃ F SO₂CH₃ 6-905 n-Pr CF₃ SMe SO₂CH₃ 6-906 n-Pr CF₃ SEt SO₂CH₃ 6-907 n-Pr CF₃ S(O)Et SO₂CH₃ 6-908 n-Pr CF₃ SO₂CH₃ SO₂CH₃ 6-909 n-Pr CF₃ OCH₂CH₂OMe SO₂CH₃ 6-910 n-Pr CF₃ OCH₂(CO)NMe₂ SO2Me 6-911 n-Pr CF₃ CH₂O-tetrahydrofuran-2-yl SO₂Et 6-912 n-Pr SMe SMe F 6-913 n-Pr SMe SEt F 6-914 n-Pr SO₂CH₃ F Cl 6-915 n-Pr F S(O)Me CF₃ 6-916 n-Pr F SMe CF₃ 6-917 CH₂OEt NO₂ H SO₂Me 6-918 CH₂OEt Cl H SO₂Me 6-919 CH₂OEt SO₂Me H CF₃ 6-920 CH₂OEt NO₂ H OMe 6-921 CH₂OEt NO₂ H Br 6-922 CH₂OEt NO₂ H CF₃ 6-923 CH₂OEt NO₂ H NO₂ 6-924 CH₂OEt NO₂ H Cl 6-925 CH₂OEt NO₂ H Me 6-926 CH₂OEt NO₂ H F 6-927 CH₂OEt OMe H SO₂Me 6-928 CH₂OEt CF₃ H NO₂ 6-929 CH₂OEt CH₂SO₂Me H Br 6-930 CH₂OEt Cl CH₂OCH₂CF₃ SO₂Me 6-931 CH₂OEt Cl CH₂OCH₂CF₃ SMe 6-932 CH₂OEt Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-933 CH₂OEt Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-934 CH₂OEt Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-935 CH₂OEt Cl SMe Cl 6-936 CH₂OEt Cl SMe SO₂Me 6-937 CH₂OEt Cl Me SO₂Et 6-938 CH₂OEt Cl O(CH₂)₂OMe Cl 6-939 CH₂OEt Cl OCH₂-cyclopropyl Cl 6-940 CH₂OEt Cl OMe Cl 6-941 CH₂OEt Cl NHAc Cl 6-942 CH₂OEt Cl OCH₂C(O)NMe₂ Cl 6-943 CH₂OEt Cl Cl SO₂Me 6-944 CH₂OEt Cl pyrazol-1-yl SO₂Me 6-945 CH₂OEt Cl 4-methoxypyrazol-1-yl SO₂Me 6-946 CH₂OEt Cl 1,2,3-triazol-1-yl SO₂Me 6-947 CH₂OEt Cl 1,2,3-triazol-2-yl SO₂Me 6-948 CH₂OEt Cl F SO₂Me 6-949 CH₂OEt Me SO₂Me SO₂Me 6-950 CH₂OEt Me SO₂Me CF₃ 6-951 CH₂OEt Me NMe₂ SO₂Me 6-952 CH₂OEt Me S(O)Me CF₃ 6-953 CH₂OEt Me SMe CF₃ 6-954 CH₂OEt Me SO₂CH₂CH₂OMe CF₃ 6-955 CH₂OEt Me pyrazol-1-yl SO₂Me 6-956 CH₂OEt Me 4-methoxypyrazol-1-yl SO₂Me 6-957 CH₂OEt Me 1,2,3-triazol-1-yl SO₂Me 6-958 CH₂OEt Me 1,2,3-triazol-2-yl SO₂Me 6-959 CH₂OEt Me Cl SO₂Me 6-960 CH₂OEt Me Me SO₂Me 6-961 CH₂OEt Me Me SMe 6-962 CH₂OEt Me SO₂Me Cl 6-963 CH₂OEt Me NMe₂ SO₂Me 6-964 CH₂OEt Me NH(CH₂)₂OMe SO₂Me 6-965 CH₂OEt CF₃ F SO₂CH₃ 6-966 CH₂OEt CF₃ SMe SO₂CH₃ 6-967 CH₂OEt CF₃ SEt SO₂CH₃ 6-968 CH₂OEt CF₃ S(O)Et SO₂CH₃ 6-969 CH₂OEt CF₃ SO₂CH₃ SO₂CH₃ 6-970 CH₂OEt CF₃ OCH₂CH₂OMe SO₂CH₃ 6-971 CH₂OEt CF₃ OCH₂(CO)NMe₂ SO2Me 6-972 CH₂OEt CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-973 CH₂OEt SMe SMe F 6-974 CH₂OEt SMe SEt F 6-975 CH₂OEt SO₂CH₃ F Cl 6-976 CH₂OEt F S(O)Me CF₃ 6-977 CH₂OEt F SMe CF₃ 6-978 cyclobutyl NO₂ H SO₂Me 6-979 cyclobutyl Cl H SO₂Me 6-980 cyclobutyl SO₂Me H CF₃ 6-981 cyclobutyl NO₂ H OMe 6-982 cyclobutyl NO₂ H Br 6-983 cyclobutyl SMe H CF₃ 6-984 cyclobutyl NO₂ H NO₂ 6-985 cyclobutyl NO₂ H Cl 6-986 cyclobutyl NO₂ H Me 6-987 cyclobutyl NO₂ H F 6-988 cyclobutyl OMe H SO₂Me 6-989 cyclobutyl CF₃ H NO₂ 6-990 cyclobutyl CH₂SO₂Me H Br 6-991 cyclobutyl Cl CH₂OCH₂CF₃ SO₂Me 6-992 cyclobutyl Cl CH₂OCH₂CF₃ SMe 6-993 cyclobutyl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-994 cyclobutyl Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-995 cyclobutyl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-996 cyclobutyl Cl SMe Cl 6-997 cyclobutyl Cl SMe SO₂Me 6-998 cyclobutyl Cl Me SO₂Et 6-999 cyclobutyl Cl O(CH₂)₂OMe Cl 6-1000 cyclobutyl Cl OCH₂-cyclopropyl Cl 6-1001 cyclobutyl Cl OMe Cl 6-1002 cyclobutyl Cl NHAc Cl 6-1003 cyclobutyl Cl OCH₂C(O)NMe₂ Cl 6-1004 cyclobutyl Cl Cl SO₂Me 6-1005 cyclobutyl Cl pyrazol-1-yl SO₂Me 6-1006 cyclobutyl Cl 4-methoxypyrazol-1-yl SO₂Me 6-1007 cyclobutyl Cl 1,2,3-triazol-1-yl SO₂Me 6-1008 cyclobutyl Cl 1,2,3-triazol-2-yl SO₂Me 6-1009 cyclobutyl Cl F SO₂Me 6-1010 cyclobutyl Me SO₂Me SO₂Me 6-1011 cyclobutyl Me SO₂Me CF₃ 6-1012 cyclobutyl Me NMe₂ SO₂Me 6-1013 cyclobutyl Me S(O)Me CF₃ 6-1014 cyclobutyl Me SMe CF₃ 6-1015 cyclobutyl Me SO₂CH₂CH₂OMe CF₃ 6-1016 cyclobutyl Me pyrazol-1-yl SO₂Me 6-1017 cyclobutyl Me 4-methoxypyrazol-1-yl SO₂Me 6-1018 cyclobutyl Me 1,2,3-triazol-1-yl SO₂Me 6-1019 cyclobutyl Me 1,2,3-triazol-2-yl SO₂Me 6-1020 cyclobutyl Me Cl SO₂Me 6-1021 cyclobutyl Me Me SO₂Me 6-1022 cyclobutyl Me Me SMe 6-1023 cyclobutyl Me SO₂Me Cl 6-1024 cyclobutyl Me NMe₂ SO₂Me 6-1025 cyclobutyl Me NH(CH₂)₂OMe SO₂Me 6-1026 cyclobutyl CF₃ F SO₂CH₃ 6-1027 cyclobutyl CF₃ SMe SO₂CH₃ 6-1028 cyclobutyl CF₃ SEt SO₂CH₃ 6-1029 cyclobutyl CF₃ S(O)Et SO₂CH₃ 6-1030 cyclobutyl CF₃ SO₂CH₃ SO₂CH₃ 6-1031 cyclobutyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1032 cyclobutyl CF₃ OCH₂(CO)NMe₂ SO2Me 6-1033 cyclobutyl CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-1034 cyclobutyl SMe SMe F 6-1035 cyclobutyl SMe SEt F 6-1036 cyclobutyl SO₂CH₃ F Cl 6-1037 cyclobutyl F S(O)Me CF₃ 6-1038 cyclobutyl F SMe CF₃ 6-1039 cyclopentyl NO₂ H SO₂Me 6-1040 cyclopentyl Cl H SO₂Me 6-1041 cyclopentyl SO₂Me H CF₃ 6-1042 cyclopentyl NO₂ H OMe 6-1043 cyclopentyl NO₂ H Br 6-1044 cyclopentyl SMe H CF₃ 6-1045 cyclopentyl NO₂ H NO₂ 6-1046 cyclopentyl NO₂ H Cl 6-1047 cyclopentyl NO₂ H Me 6-1048 cyclopentyl NO₂ H F 6-1049 cyclopentyl OMe H SO₂Me 6-1050 cyclopentyl CF₃ H NO₂ 6-1051 cyclopentyl CH₂SO₂Me H Br 6-1052 cyclopentyl Cl CH₂OCH₂CF₃ SO₂Me 6-1053 cyclopentyl Cl CH₂OCH₂CF₃ SMe 6-1054 cyclopentyl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-1055 cyclopentyl Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-1056 cyclopentyl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-1057 cyclopentyl Cl SMe Cl 6-1058 cyclopentyl Cl SMe SO₂Me 6-1059 cyclopentyl Cl Me SO₂Et 6-1060 cyclopentyl Cl O(CH₂)₂OMe Cl 6-1061 cyclopentyl Cl OCH₂-cyclopropyl Cl 6-1062 cyclopentyl Cl OMe Cl 6-1063 cyclopentyl Cl NHAc Cl 6-1064 cyclopentyl Cl OCH₂C(O)NMe₂ Cl 6-1065 cyclopentyl Cl Cl SO₂Me 6-1066 cyclopentyl Cl pyrazol-1-yl SO₂Me 6-1067 cyclopentyl Cl 4-methoxypyrazol-1-yl SO₂Me 6-1068 cyclopentyl Cl 1,2,3-triazol-1-yl SO₂Me 6-1069 cyclopentyl Cl 1,2,3-triazol-2-yl SO₂Me 6-1070 cyclopentyl Cl F SO₂Me 6-1071 cyclopentyl Me SO₂Me SO₂Me 6-1072 cyclopentyl Me SO₂Me CF₃ 6-1073 cyclopentyl Me NMe₂ SO₂Me 6-1074 cyclopentyl Me S(O)Me CF₃ 6-1075 cyclopentyl Me SMe CF₃ 6-1076 cyclopentyl Me SO₂CH₂CH₂OMe CF₃ 6-1077 cyclopentyl Me pyrazol-1-yl SO₂Me 6-1078 cyclopentyl Me 4-methoxypyrazol-1-yl SO₂Me 6-1079 cyclopentyl Me 1,2,3-triazol-1-yl SO₂Me 6-1080 cyclopentyl Me 1,2,3-triazol-2-yl SO₂Me 6-1081 cyclopentyl Me Cl SO₂Me 6-1082 cyclopentyl Me Me SO₂Me 6-1083 cyclopentyl Me Me SMe 6-1084 cyclopentyl Me SO₂Me Cl 6-1085 cyclopentyl Me NMe₂ SO₂Me 6-1086 cyclopentyl Me NH(CH₂)₂OMe SO₂Me 6-1087 cyclopentyl CF₃ F SO₂CH₃ 6-1088 cyclopentyl CF₃ SMe SO₂CH₃ 6-1089 cyclopentyl CF₃ SEt SO₂CH₃ 6-1090 cyclopentyl CF₃ S(O)Et SO₂CH₃ 6-1091 cyclopentyl CF₃ SO₂CH₃ SO₂CH₃ 6-1092 cyclopentyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1093 cyclopentyl CF₃ OCH₂(CO)NMe₂ SO2Me 6-1094 cyclopentyl CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-1095 cyclopentyl SMe SMe F 6-1096 cyclopentyl SMe SEt F 6-1097 cyclopentyl SO₂CH₃ F Cl 6-1098 cyclopentyl F S(O)Me CF₃ 6-1099 cyclopentyl F SMe CF₃ 6-1100 Me₂N NO₂ H SO₂Me 6-1101 Me₂N Cl H SO₂Me 6-1102 Me₂N SO₂Me H CF₃ 6-1103 Me₂N NO₂ H OMe 6-1104 Me₂N NO₂ H Br 6-1105 Me₂N NO₂ H CF₃ 6-1106 Me₂N NO₂ H NO₂ 6-1107 Me₂N NO₂ H Cl 6-1108 Me₂N NO₂ H Me 6-1109 Me₂N NO₂ H F 6-1110 Me₂N OMe H SO₂Me 6-1111 Me₂N CF₃ H NO₂ 6-1112 Me₂N CH₂SO₂Me H Br 6-1113 Me₂N Cl CH₂OCH₂CF₃ SO₂Me 6-1114 Me₂N Cl CH₂OCH₂CF₃ SMe 6-1115 Me₂N Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-1116 Me₂N Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-1117 Me₂N Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-1118 Me₂N Cl SMe Cl 6-1119 Me₂N Cl SMe SO₂Me 6-1120 Me₂N Cl Me SO₂Et 6-1121 Me₂N Cl O(CH₂)₂OMe Cl 6-1122 Me₂N Cl OCH₂- Cl cyclopropyl 6-1123 Me₂N Cl OMe Cl 6-1124 Me₂N Cl NHAc Cl 6-1125 Me₂N Cl OCH₂C(O)NMe₂ Cl 6-1126 Me₂N Cl Cl SO₂Me 6-1127 Me₂N Cl pyrazol-1-yl SO₂Me 6-1128 Me₂N Cl 4-methoxypyrazol-1-yl SO₂Me 6-1129 Me₂N Cl 1,2,3-triazol-1-yl SO₂Me 6-1130 Me₂N Cl 1,2,3-triazol-2-yl SO₂Me 6-1131 Me₂N Cl F SO₂Me 6-1132 Me₂N Me SO₂Me SO₂Me 6-1133 Me₂N Me SO₂Me CF₃ 6-1134 Me₂N Me NMe₂ SO₂Me 6-1135 Me₂N Me S(O)Me CF₃ 6-1136 Me₂N Me SMe CF₃ 6-1137 Me₂N Me SO₂CH₂CH₂OMe CF₃ 6-1138 Me₂N Me pyrazol-1-yl SO₂Me 6-1139 Me₂N Me 4-methoxypyrazol-1-yl SO₂Me 6-1140 Me₂N Me 1,2,3-triazol-1-yl SO₂Me 6-1141 Me₂N Me 1,2,3-triazol-2-yl SO₂Me 6-1142 Me₂N Me Cl SO₂Me 6-1143 Me₂N Me Me SO₂Me 6-1144 Me₂N Me Me SMe 6-1145 Me₂N Me SO₂Me Cl 6-1146 Me₂N Me NMe₂ SO₂Me 6-1147 Me₂N Me NH(CH₂)₂OMe SO₂Me 6-1148 Me₂N CF₃ F SO₂CH₃ 6-1149 Me₂N CF₃ SMe SO₂CH₃ 6-1150 Me₂N CF₃ SEt SO₂CH₃ 6-1151 Me₂N CF₃ S(O)Et SO₂CH₃ 6-1152 Me₂N CF₃ SO₂CH₃ SO₂CH₃ 6-1153 Me₂N CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1154 Me₂N CF₃ OCH₂(CO)NMe₂ SO2Me 6-1155 Me₂N CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-1156 Me₂N SMe SMe F 6-1157 Me₂N SMe SEt F 6-1158 Me₂N SO₂CH₃ F Cl 6-1159 Me₂N F S(O)Me CF₃ 6-1160 Me₂N F SMe CF₃ 6-1161 Ph—NH NO₂ H SO₂Me 6-1162 Ph—NH Cl H SO₂Me 6-1163 Ph—NH SO₂Me H CF₃ 6-1164 Ph—NH NO₂ H OMe 6-1165 Ph—NH NO₂ H Br 6-1166 Ph—NH NO₂ H CF₃ 6-1167 Ph—NH NO₂ H NO₂ 6-1168 Ph—NH NO₂ H Cl 6-1169 Ph—NH NO₂ H Me 6-1170 Ph—NH NO₂ H F 6-1171 Ph—NH OMe H SO₂Me 6-1172 Ph—NH CF₃ H NO₂ 6-1173 Ph—NH CH₂SO₂Me H Br 6-1174 Ph—NH Cl CH₂OCH₂CF₃ SO₂Me 6-1175 Ph—NH Cl CH₂OCH₂CF₃ SMe 6-1176 Ph—NH Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-1177 Ph—NH Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-1178 Ph—NH Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-1179 Ph—NH Cl SMe Cl 6-1180 Ph—NH Cl SMe SO₂Me 6-1181 Ph—NH Cl Me SO₂Et 6-1182 Ph—NH Cl O(CH₂)₂OMe Cl 6-1183 Ph—NH Cl OCH₂-cyclopropyl Cl 6-1184 Ph—NH Cl OMe Cl 6-1185 Ph—NH Cl NHAc Cl 6-1186 Ph—NH Cl OCH₂C(O)NMe₂ Cl 6-1187 Ph—NH Cl Cl SO₂Me 6-1188 Ph—NH Cl pyrazol-1-yl SO₂Me 6-1189 Ph—NH Cl 4-methoxypyrazol-1-yl SO₂Me 6-1190 Ph—NH Cl 1,2,3-triazol-1-yl SO₂Me 6-1191 Ph—NH Cl 1,2,3-triazol-2-yl SO₂Me 6-1192 Ph—NH Cl F SO₂Me 6-1193 Ph—NH Me SO₂Me SO₂Me 6-1194 Ph—NH Me SO₂Me CF₃ 6-1195 Ph—NH Me NMe₂ SO₂Me 6-1196 Ph—NH Me S(O)Me CF₃ 6-1197 Ph—NH Me SMe CF₃ 6-1198 Ph—NH Me SO₂CH₂CH₂OMe CF₃ 6-1199 Ph—NH Me pyrazol-1-yl SO₂Me 6-1200 Ph—NH Me 4-methoxypyrazol-1-yl SO₂Me 6-1201 Ph—NH Me 1,2,3-triazol-1-yl SO₂Me 6-1202 Ph—NH Me 1,2,3-triazol-2-yl SO₂Me 6-1203 Ph—NH Me Cl SO₂Me 6-1204 Ph—NH Me Me SO₂Me 6-1205 Ph—NH Me Me SMe 6-1206 Ph—NH Me SO₂Me Cl 6-1207 Ph—NH Me NMe₂ SO₂Me 6-1208 Ph—NH Me NH(CH₂)₂OMe SO₂Me 6-1209 Ph—NH CF₃ F SO₂CH₃ 6-1210 Ph—NH CF₃ SMe SO₂CH₃ 6-1211 Ph—NH CF₃ SEt SO₂CH₃ 6-1212 Ph—NH CF₃ S(O)Et SO₂CH₃ 6-1213 Ph—NH CF₃ SO₂CH₃ SO₂CH₃ 6-1214 Ph—NH CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1215 Ph—NH CF₃ OCH₂(CO)NMe₂ SO2Me 6-1216 Ph—NH CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-1217 Ph—NH SMe SMe F 6-1218 Ph—NH SMe SEt F 6-1219 Ph—NH SO₂CH₃ F Cl 6-1220 Ph—NH F S(O)Me CF₃ 6-1221 Ph—NH F SMe CF₃ 6-1222 morpholin-1-yl NO₂ H SO₂Me 6-1223 morpholin-1-yl Cl H SO₂Me 6-1224 morpholin-1-yl SO₂Me H CF₃ 6-1225 morpholin-1-yl NO₂ H OMe 6-1226 morpholin-1-yl NO₂ H Br 6-1227 morpholin-1-yl NO₂ H CF₃ 6-1228 morpholin-1-yl NO₂ H NO₂ 6-1229 morpholin-1-yl NO₂ H Cl 6-1230 morpholin-1-yl NO₂ H Me 6-1231 morpholin-1-yl NO₂ H F 6-1232 morpholin-1-yl OMe H SO₂Me 6-1233 morpholin-1-yl CF₃ H NO₂ 6-1234 morpholin-1-yl CH₂SO₂Me H Br 6-1235 morpholin-1-yl Cl CH₂OCH₂CF₃ SO₂Me 6-1236 morpholin-1-yl Cl CH₂OCH₂CF₃ SMe 6-1237 morpholin-1-yl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-1238 morpholin-1-yl Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-1239 morpholin-1-yl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-1240 morpholin-1-yl Cl SMe Cl 6-1241 morpholin-1-yl Cl SMe SO₂Me 6-1242 morpholin-1-yl Cl Me SO₂Et 6-1243 morpholin-1-yl Cl O(CH₂)₂OMe Cl 6-1244 morpholin-1-yl Cl OCH₂-cyclopropyl Cl 6-1245 morpholin-1-yl Cl OMe Cl 6-1246 morpholin-1-yl Cl NHAc Cl 6-1247 morpholin-1-yl Cl OCH₂C(O)NMe₂ Cl 6-1248 morpholin-1-yl Cl Cl SO₂Me 6-1249 morpholin-1-yl Cl pyrazol-1-yl SO₂Me 6-1250 morpholin-1-yl Cl 4-methoxypyrazol-1-yl SO₂Me 6-1251 morpholin-1-yl Cl 1,2,3-triazol-1-yl SO₂Me 6-1252 morpholin-1-yl Cl 1,2,3-triazol-2-yl SO₂Me 6-1253 morpholin-1-yl Cl F SO₂Me 6-1254 morpholin-1-yl Me SO₂Me SO₂Me 6-1255 morpholin-1-yl Me SO₂Me CF₃ 6-1256 morpholin-1-yl Me NMe₂ SO₂Me 6-1257 morpholin-1-yl Me S(O)Me CF₃ 6-1258 morpholin-1-yl Me SMe CF₃ 6-1259 morpholin-1-yl Me SO₂CH₂CH₂OMe CF₃ 6-1260 morpholin-1-yl Me pyrazol-1-yl SO₂Me 6-1261 morpholin-1-yl Me 4-methoxypyrazol-1-yl SO₂Me 6-1262 morpholin-1-yl Me 1,2,3-triazol-1-yl SO₂Me 6-1263 morpholin-1-yl Me 1,2,3-triazol-2-yl SO₂Me 6-1264 morpholin-1-yl Me Cl SO₂Me 6-1265 morpholin-1-yl Me Me SO₂Me 6-1266 morpholin-1-yl Me Me SMe 6-1267 morpholin-1-yl Me SO₂Me Cl 6-1268 morpholin-1-yl Me NMe₂ SO₂Me 6-1269 morpholin-1-yl Me NH(CH₂)₂OMe SO₂Me 6-1270 morpholin-1-yl CF₃ F SO₂CH₃ 6-1271 morpholin-1-yl CF₃ SMe SO₂CH₃ 6-1272 morpholin-1-yl CF₃ SEt SO₂CH₃ 6-1273 morpholin-1-yl CF₃ S(O)Et SO₂CH₃ 6-1274 morpholin-1-yl CF₃ SO₂CH₃ SO₂CH₃ 6-1275 morpholin-1-yl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1276 morpholin-1-yl CF₃ OCH₂(CO)NMe₂ SO2Me 6-1277 morpholin-1-yl CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-1278 morpholin-1-yl SMe SMe F 6-1279 morpholin-1-yl SMe SEt F 6-1280 morpholin-1-yl SO₂CH₃ F Cl 6-1281 morpholin-1-yl F S(O)Me CF₃ 6-1282 morpholin-1-yl F SMe CF₃ 6-1283 sec-Bu NO₂ H SO₂Me 6-1284 sec-Bu Cl H SO₂Me 6-1285 sec-Bu SO₂Me H CF₃ 6-1286 sec-Bu NO₂ H OMe 6-1287 sec-Bu NO₂ H Br 6-1288 sec-Bu NO₂ H CF₃ 6-1289 sec-Bu NO₂ H NO₂ 6-1290 sec-Bu NO₂ H Cl 6-1291 sec-Bu NO₂ H Me 6-1292 sec-Bu NO₂ H F 6-1293 sec-Bu OMe H SO₂Me 6-1294 sec-Bu CF₃ H NO₂ 6-1295 sec-Bu CH₂SO₂Me H Br 6-1296 sec-Bu Cl CH₂OCH₂CF₃ SO₂Me 6-1297 sec-Bu Cl CH₂OCH₂CF₃ SMe 6-1298 sec-Bu Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-1299 sec-Bu Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 6-1300 sec-Bu Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-1301 sec-Bu Cl SMe Cl 6-1302 sec-Bu Cl SMe SO₂Me 6-1303 sec-Bu Cl Me SO₂Et 6-1304 sec-Bu Cl O(CH₂)₂OMe Cl 6-1305 sec-Bu Cl OCH₂-cyclopropyl Cl 6-1306 sec-Bu Cl OMe Cl 6-1307 sec-Bu Cl NHAc Cl 6-1308 sec-Bu Cl OCH₂C(O)NMe₂ Cl 6-1309 sec-Bu Cl Cl SO₂Me 6-1310 sec-Bu Cl pyrazol-1-yl SO₂Me 6-1311 sec-Bu Cl 4-methoxypyrazol-1-yl SO₂Me 6-1312 sec-Bu Cl 1,2,3-triazol-1-yl SO₂Me 6-1313 sec-Bu Cl 1,2,3-triazol-2-yl SO₂Me 6-1314 sec-Bu Cl F SO₂Me 6-1315 sec-Bu Me SO₂Me SO₂Me 6-1316 sec-Bu Me SO₂Me CF₃ 6-1317 sec-Bu Me NMe₂ SO₂Me 6-1318 sec-Bu Me S(O)Me CF₃ 6-1319 sec-Bu Me SMe CF₃ 6-1320 sec-Bu Me SO₂CH₂CH₂OMe CF₃ 6-1321 sec-Bu Me pyrazol-1-yl SO₂Me 6-1322 sec-Bu Me 4-methoxypyrazol-1-yl SO₂Me 6-1323 sec-Bu Me 1,2,3-triazol-1-yl SO₂Me 6-1324 sec-Bu Me 1,2,3-triazol-2-yl SO₂Me 6-1325 sec-Bu Me Cl SO₂Me 6-1326 sec-Bu Me Me SO₂Me 6-1327 sec-Bu Me Me SMe 6-1328 sec-Bu Me SO₂Me Cl 6-1329 sec-Bu Me NMe₂ SO₂Me 6-1330 sec-Bu Me NH(CH₂)₂OMe SO₂Me 6-1331 sec-Bu CF₃ F SO₂CH₃ 6-1332 sec-Bu CF₃ SMe SO₂CH₃ 6-1333 sec-Bu CF₃ SEt SO₂CH₃ 6-1334 sec-Bu CF₃ S(O)Et SO₂CH₃ 6-1335 sec-Bu CF₃ SO₂CH₃ SO₂CH₃ 6-1336 sec-Bu CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1337 sec-Bu CF₃ OCH₂(CO)NMe₂ SO₂Me 6-1338 sec-Bu CF₃ CH₂O- SO2Et tetrahydrofuran-2-yl 6-1339 sec-Bu SMe SMe F 6-1340 sec-Bu SMe SEt F 6-1341 sec-Bu SO₂CH₃ F Cl 6-1342 sec-Bu F S(O)Me CF₃ 6-1343 sec-Bu F SMe CF₃

TABLE 7 Compounds of the general formula (I) according to the invention in which A represents nitrogen, V represents hydrogen, W represents fluorine

Physical data (¹H-NMR, DMSO-d₆, No. R X Z 400 MHz) 7-1 H Cl CF₃ 7-2 Me Cl CF₃ 7-3 Et Cl CF₃ 7-4 CF₃ Cl CF₃ 7-5 CH₂OMe Cl CF₃ 7-6 c-Pr Cl CF₃ 7-7 CO₂Et Cl CF₃ 7-8 CO₂Me Cl CF₃ 7-9 benzyl Cl CF₃ 7-10 phenyl Cl CF₃ 7-11 pyrazin-2-yl Cl CF₃ 7-12 4-OMe—Ph Cl CF₃ 7-13 4-Cl—Ph Cl CF₃ 7-14 t-Bu Cl CF₃ 7-15 furan-2-yl Cl CF₃ 7-16 i-Pr Cl CF₃ 7-17 CH₂CH₂OMe Cl CF₃ 7-18 CH₂CF₃ Cl CF₃ 7-19 tetrahydrofuran- Cl CF₃ 2-yl 7-20 n-Pr Cl CF₃ 7-21 CH₂OEt Cl CF₃ 7-22 cyclobutyl Cl CF₃ 7-23 cyclopentyl Cl CF₃ 7-24 Me₂N Cl CF₃ 7-25 Ph—NH Cl CF₃ 7-26 morpholin-1-yl Cl CF₃ 7-27 H Cl Cl 7-28 Me Cl Cl 7-29 Et Cl Cl 7-30 CF₃ Cl Cl 7-31 CH₂OMe Cl Cl 7-32 c-Pr Cl Cl 7-33 CO₂Et Cl Cl 7-34 CO₂Me Cl Cl 7-35 benzyl Cl Cl 7-36 phenyl Cl Cl 7-37 pyrazin-2-yl Cl Cl 7-38 4-OMe—Ph Cl Cl 7-39 4-Cl—Ph Cl Cl 7-40 t-Bu Cl Cl 7-41 furan-2-yl Cl Cl 7-42 i-Pr Cl Cl 7-43 CH₂CH₂OMe Cl Cl 7-44 CH₂CF₃ Cl Cl 7-45 tetrahydrofuran- Cl Cl 2-yl 7-46 n-Pr Cl Cl 7-47 CH₂OEt Cl Cl 7-48 cyclobutyl Cl Cl 7-49 cyclopentyl Cl Cl 7-50 Me₂N Cl Cl 7-51 Ph—NH Cl Cl 7-52 morpholin-1-yl Cl Cl 7-53 H Me Cl 7-54 Me Me Cl 7-55 Et Me Cl 7-56 CF₃ Me Cl 7-57 CH₂OMe Me Cl 7-58 c-Pr Me Cl 7-59 CO₂Et Me Cl 7-60 CO₂Me Me Cl 7-61 benzyl Me Cl 7-62 phenyl Me Cl 7-63 pyrazin-2-yl Me Cl 7-64 4-OMe—Ph Me Cl 7-65 4-Cl—Ph Me Cl 7-66 t-Bu Me Cl 7-67 furan-2-yl Me Cl 7-68 i-Pr Me Cl 7-69 CH₂CH₂OMe Me Cl 7-70 CH₂CF₃ Me Cl 7-71 tetrahydrofuran- Me Cl 2-yl 7-72 n-Pr Me Cl 7-73 CH₂OEt Me Cl 7-74 cyclobutyl Me Cl 7-75 cyclopentyl Me Cl 7-76 Me₂N Me Cl 7-77 Ph—NH Me Cl 7-78 morpholin-1-yl Me Cl 7-79 H Cl SMe 7-80 Me Cl SMe 7-81 Et Cl SMe 7-82 CF₃ Cl SMe 7-83 CH₂OMe Cl SMe 7-84 c-Pr Cl SMe 7-85 CO₂Et Cl SMe 7-86 CO₂Me Cl SMe 7-87 benzyl Cl SMe 7-88 phenyl Cl SMe 7-89 pyrazin-2-yl Cl SMe 7-90 4-OMe—Ph Cl SMe 7-91 4-Cl—Ph Cl SMe 7-92 t-Bu Cl SMe 7-93 furan-2-yl Cl SMe 7-94 i-Pr Cl SMe 7-95 CH₂CH₂OMe Cl SMe 7-96 CH₂CF₃ Cl SMe 7-97 tetrahydrofuran- Cl SMe 2-yl 7-98 n-Pr Cl SMe 7-99 CH₂OEt Cl SMe 7-100 cyclobutyl Cl SMe 7-101 cyclopentyl Cl SMe 7-102 Me₂N Cl SMe 7-103 Ph—NH Cl SMe 7-104 morpholin-1-yl Cl SMe 7-105 H Cl SO₂Me 7-106 Me Cl SO₂Me 7-107 Et Cl SO₂Me 7-108 CF₃ Cl SO₂Me 7-109 CH₂OMe Cl SO₂Me 7-110 c-Pr Cl SO₂Me 7-111 CO₂Et Cl SO₂Me 7-112 CO₂Me Cl SO₂Me 7-113 benzyl Cl SO₂Me 7-114 phenyl Cl SO₂Me 7-115 pyrazin-2-yl Cl SO₂Me 7-116 4-OMe—Ph Cl SO₂Me 7-117 4-Cl—Ph Cl SO₂Me 7-118 t-Bu Cl SO₂Me 7-119 furan-2-yl Cl SO₂Me 7-120 i-Pr Cl SO₂Me 7-121 CH₂CH₂OMe Cl SO₂Me 7-122 CH₂CF₃ Cl SO₂Me 7-123 tetrahydrofuran- Cl SO₂Me 2-yl 7-124 n-Pr Cl SO₂Me 7-125 CH₂OEt Cl SO₂Me 7-126 cyclobutyl Cl SO₂Me 7-127 cyclopentyl Cl SO₂Me 7-128 Me₂N Cl SO₂Me 7-129 Ph—NH Cl SO₂Me 7-130 morpholin-1-yl Cl SO₂Me 7-131 H Me CF₃ 7-132 Me Me CF₃ 7-133 Et Me CF₃ 7-134 CF₃ Me CF₃ 7-135 CH₂OMe Me CF₃ 7-136 c-Pr Me CF₃ 7-137 CO₂Et Me CF₃ 7-138 CO₂Me Me CF₃ 7-139 benzyl Me CF₃ 7-140 phenyl Me CF₃ 7-141 pyrazin-2-yl Me CF₃ 7-142 4-OMe—Ph Me CF₃ 7-143 4-Cl—Ph Me CF₃ 7-144 t-Bu Me CF₃ 7-145 furan-2-yl Me CF₃ 7-146 i-Pr Me CF₃ 7-147 CH₂CH₂OMe Me CF₃ 7-148 CH₂CF₃ Me CF₃ 7-149 tetrahydrofuran- Me CF₃ 2-yl 7-150 n-Pr Me CF₃ 7-151 CH₂OEt Me CF₃ 7-152 cyclobutyl Me CF₃ 7-153 cyclopentyl Me CF₃ 7-154 Me₂N Me CF₃ 7-155 Ph—NH Me CF₃ 7-156 morpholin-1-yl Me CF₃ 7-157 H CH₂OMe CF₃ 7-158 Me CH₂OMe CF₃ 7-159 Et CH₂OMe CF₃ 7-160 CF₃ CH₂OMe CF₃ 7-161 CH₂OMe CH₂OMe CF₃ 7-162 c-Pr CH₂OMe CF₃ 7-163 CO₂Et CH₂OMe CF₃ 7-164 CO₂Me CH₂OMe CF₃ 7-165 benzyl CH₂OMe CF₃ 7-166 phenyl CH₂OMe CF₃ 7-167 pyrazin-2-yl CH₂OMe CF₃ 7-168 4-OMe—Ph CH₂OMe CF₃ 7-169 4-Cl—Ph CH₂OMe CF₃ 7-170 t-Bu CH₂OMe CF₃ 7-171 furan-2-yl CH₂OMe CF₃ 7-172 i-Pr CH₂OMe CF₃ 7-173 CH₂CH₂OMe CH₂OMe CF₃ 7-174 CH₂CF₃ CH₂OMe CF₃ 7-175 tetrahydrofuran- CH₂OMe CF₃ 2-yl 7-176 n-Pr CH₂OMe CF₃ 7-177 CH₂OEt CH₂OMe CF₃ 7-178 cyclobutyl CH₂OMe CF₃ 7-179 cyclopentyl CH₂OMe CF₃ 7-180 Me₂N CH₂OMe CF₃ 7-181 Ph—NH CH₂OMe CF₃ 7-182 morpholin-1-yl CH₂OMe CF₃ 7-183 H CH₂SMe CF₃ 7-184 Me CH₂SMe CF₃ 7-185 Et CH₂SMe CF₃ 7-186 CF₃ CH₂SMe CF₃ 7-187 CH₂OMe CH₂SMe CF₃ 7-188 c-Pr CH₂SMe CF₃ 7-189 CO₂Et CH₂SMe CF₃ 7-190 CO₂Me CH₂SMe CF₃ 7-191 benzyl CH₂SMe CF₃ 7-192 phenyl CH₂SMe CF₃ 7-193 pyrazin-2-yl CH₂SMe CF₃ 7-194 4-OMe—Ph CH₂SMe CF₃ 7-195 4-Cl—Ph CH₂SMe CF₃ 7-196 t-Bu CH₂SMe CF₃ 7-197 furan-2-yl CH₂SMe CF₃ 7-198 i-Pr CH₂SMe CF₃ 7-199 CH₂CH₂OMe CH₂SMe CF₃ 7-200 CH₂CF₃ CH₂SMe CF₃ 7-201 tetrahydrofuran- CH₂SMe CF₃ 2-yl 7-202 n-Pr CH₂SMe CF₃ 7-203 CH₂OEt CH₂SMe CF₃ 7-204 cyclobutyl CH₂SMe CF₃ 7-205 cyclopentyl CH₂SMe CF₃ 7-206 Me₂N CH₂SMe CF₃ 7-207 Ph—NH CH₂SMe CF₃ 7-208 morpholin-1-yl CH₂SMe CF₃ 7-209 H CH₂SO₂Me CF₃ 7-210 Me CH₂SO₂Me CF₃ 7-211 Et CH₂SO₂Me CF₃ 7-212 CF₃ CH₂SO₂Me CF₃ 7-213 CH₂OMe CH₂SO₂Me CF₃ 7-214 c-Pr CH₂SO₂Me CF₃ 7-215 CO₂Et CH₂SO₂Me CF₃ 7-216 CO₂Me CH₂SO₂Me CF₃ 7-217 benzyl CH₂SO₂Me CF₃ 7-218 phenyl CH₂SO₂Me CF₃ 7-219 pyrazin-2-yl CH₂SO₂Me CF₃ 7-220 4-OMe—Ph CH₂SO₂Me CF₃ 7-221 4-Cl—Ph CH₂SO₂Me CF₃ 7-222 t-Bu CH₂SO₂Me CF₃ 7-223 furan-2-yl CH₂SO₂Me CF₃ 7-224 i-Pr CH₂SO₂Me CF₃ 7-225 CH₂CH₂OMe CH₂SO₂Me CF₃ 7-226 CH₂CF₃ CH₂SO₂Me CF₃ 7-227 tetrahydrofuran- CH₂SO₂Me CF₃ 2-yl 7-228 n-Pr CH₂SO₂Me CF₃ 7-229 CH₂OEt CH₂SO₂Me CF₃ 7-230 cyclobutyl CH₂SO₂Me CF₃ 7-231 cyclopentyl CH₂SO₂Me CF₃ 7-232 Me₂N CH₂SO₂Me CF₃ 7-233 Ph—NH CH₂SO₂Me CF₃ 7-234 morpholin-1-yl CH₂SO₂Me CF₃ 7-235 H CH₂OC₂H₄OMe CF₃ 7-236 Me CH₂OC₂H₄OMe CF₃ 7-237 Et CH₂OC₂H₄OMe CF₃ 7-238 CF₃ CH₂OC₂H₄OMe CF₃ 7-239 CH₂OMe CH₂OC₂H₄OMe CF₃ 7-240 c-Pr CH₂OC₂H₄OMe CF₃ 7-241 CO₂Et CH₂OC₂H₄OMe CF₃ 7-242 CO₂Me CH₂OC₂H₄OMe CF₃ 7-243 benzyl CH₂OC₂H₄OMe CF₃ 7-244 phenyl CH₂OC₂H₄OMe CF₃ 7-245 pyrazin-2-yl CH₂OC₂H₄OMe CF₃ 7-246 4-OMe—Ph CH₂OC₂H₄OMe CF₃ 7-247 4-Cl—Ph CH₂OC₂H₄OMe CF₃ 7-248 t-Bu CH₂OC₂H₄OMe CF₃ 7-249 furan-2-yl CH₂OC₂H₄OMe CF₃ 7-250 i-Pr CH₂OC₂H₄OMe CF₃ 7-251 CH₂CH₂OMe CH₂OC₂H₄OMe CF₃ 7-252 CH₂CF₃ CH₂OC₂H₄OMe CF₃ 7-253 tetrahydrofuran- CH₂OC₂H₄OMe CF₃ 2-yl 7-254 n-Pr CH₂OC₂H₄OMe CF₃ 7-255 CH₂OEt CH₂OC₂H₄OMe CF₃ 7-256 cyclobutyl CH₂OC₂H₄OMe CF₃ 7-257 cyclopentyl CH₂OC₂H₄OMe CF₃ 7-258 Me₂N CH₂OC₂H₄OMe CF₃ 7-259 Ph—NH CH₂OC₂H₄OMe CF₃ 7-260 morpholin-1-yl CH₂OC₂H₄OMe CF₃ 7-261 H OCH₂- CF₃ tetrahydro- furan-2-yl 7-262 Me OCH₂- CF₃ tetrahydrofuran- 2-yl 7-263 Et OCH₂- CF₃ tetrahydrofuran- 2-yl 7-264 CF₃ OCH₂- CF₃ tetrahydrofuran- 2-yl 7-265 CH₂OMe OCH₂- CF₃ tetrahydrofuran- 2-yl 7-266 c-Pr OCH₂- CF₃ tetrahydrofuran- 2-yl 7-267 CO₂Et OCH₂- CF₃ tetrahydrofuran- 2-yl 7-268 CO₂Me OCH₂- CF₃ tetrahydrofuran- 2-yl 7-269 benzyl OCH₂- CF₃ tetrahydrofuran- 2-yl 7-270 phenyl OCH₂- CF₃ tetrahydrofuran- 2-yl 7-271 pyrazin-2-yl OCH₂- CF₃ tetrahydrofuran- 2-yl 7-272 4-OMe—Ph OCH₂- CF₃ tetrahydrofuran- 2-yl 7-273 4-Cl—Ph OCH₂- CF₃ tetrahydrofuran- 2-yl 7-274 t-Bu OCH₂- CF₃ tetrahydrofuran- 2-yl 7-275 furan-2-yl OCH₂- CF₃ tetrahydrofuran- 2-yl 7-276 i-Pr OCH₂- CF₃ tetrahydrofuran- 2-yl 7-277 CH₂CH₂OMe OCH₂- CF₃ tetrahydrofuran- 2-yl 7-278 CH₂CF₃ OCH₂- CF₃ tetrahydrofuran- 2-yl 7-279 tetrahydrofuran- OCH₂- CF₃ 2-yl tetrahydrofuran- 2-yl 7-280 n-Pr OCH₂- CF₃ tetrahydrofuran- 2-yl 7-281 CH₂OEt OCH₂- CF₃ tetrahydrofuran- 2-yl 7-282 cyclobutyl OCH₂- CF₃ tetrahydrofuran- 2-yl 7-283 cyclopentyl OCH₂- CF₃ tetrahydrofuran- 2-yl 7-284 Me₂N OCH₂- CF₃ tetrahydrofuran- 2-yl 7-285 Ph—NH OCH₂- CF₃ tetrahydrofuran- 2-yl 7-286 morpholin-1-yl OCH₂- CF₃ tetrahydrofuran- 2-yl 7-287 H (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-288 Me (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-289 Et (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-290 CF₃ (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-291 CH₂OMe (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-292 c-Pr (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-293 CO₂Et (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-294 CO₂Me (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-295 benzyl (1,1-dioxido- CF₃ 1,2- thiadiazolidin-1- yl)methyl 7-296 phenyl (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-297 pyrazin-2-yl (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-298 4-OMe—Ph (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-299 4-Cl—Ph (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-300 t-Bu (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-301 furan-2-yl (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-302 i-Pr (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-303 CH₂CH₂OMe (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-304 CH₂CF₃ (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-305 tetrahydrofuran- (1,1-dioxido- CF₃ 2-yl 1,2-thiadiazolidin- 1-yl)methyl 7-306 n-Pr (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-307 CH₂OEt (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-308 cyclobutyl (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-309 cyclopentyl (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-310 Me₂N (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-311 Ph—NH (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-312 morpholin-1-yl (1,1-dioxido- CF₃ 1,2-thiadiazolidin- 1-yl)methyl 7-313 H (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-314 Me (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-315 Et (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-316 CF₃ (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-317 CH₂OMe (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-318 c-Pr (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-319 CO₂Et (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-320 CO₂Me (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-321 benzyl (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-322 phenyl (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-323 pyrazin-2-yl (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-324 4-OMe—Ph (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-325 4-Cl—Ph (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-326 t-Bu (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-327 furan-2-yl (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-328 i-Pr (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-329 CH₂CH₂OMe (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-330 CH₂CF₃ (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-331 tetrahydrofuran- (3-methyl-2- CF₃ 2-yl oxoimidazolidin- 1-yl)methyl 7-332 n-Pr (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-333 CH₂OEt (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-334 cyclobutyl (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-335 cyclopentyl (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-336 Me₂N (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-337 Ph—NH (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-338 morpholin-1-yl (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-339 H (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-340 Me (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-341 Et (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-342 CF₃ (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-343 CH₂OMe (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-344 c-Pr (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-345 CO₂Et (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-346 CO₂Me (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-347 benzyl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-348 phenyl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-349 pyrazin-2-yl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-350 4-OMe—Ph (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-351 4-Cl—Ph (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-352 t-Bu (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-353 furan-2-yl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-354 i-Pr (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-355 CH₂CH₂OMe (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-356 CH₂CF₃ (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-357 tetrahydrofuran- (3-methoxy-4- CF₃ 2-yl methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-358 n-Pr (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-359 CH₂OEt (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-360 cyclobutyl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-361 cyclopentyl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-362 Me₂N (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-363 Ph—NH (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-364 morpholin-1-yl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-365 i-Pr Cl Me

TABLE 8 Compounds according to the invention of the general formula (I), in which A represents CY, Z represents trifluoromethyl and R represents methyl

No. X Y V W Physical data 8-1 Cl SOMe H Cl 8-2 Cl SOMe H Br 8-3 Cl SOMe H CN 8-4 Cl SOMe H NO₂ 8-5 Cl SOMe H Me 8-6 Cl SOMe H Et 8-7 Cl SOMe H iPr 8-8 Cl SOMe H cPr 8-9 Cl SOMe H tBu 8-10 Cl SOMe H CF₃ 8-11 Cl SOMe H CHF₂t 8-12 Cl SOMe H C₂F₅ 8-13 Cl SOMe H CH₂OMe 8-14 Cl SOMe H OMe 8-15 Cl SOMe H OEt 8-16 Cl SOMe H OCF₃ 8-17 Cl SOMe H SMe 8-18 Cl SOMe H SOMe 8-19 Cl SOMe H SO₂Me 8-20 Cl SOMe Cl H 8-21 Cl SOMe Br H 8-22 Cl SOMe CN H 8-23 Cl SOMe NO₂ H 8-24 Cl SOMe Me H 8-25 Cl SOMe Et H 8-26 Cl SOMe iPr H 8-27 Cl SOMe cPr H 8-28 Cl SOMe tBu H 8-29 Cl SOMe CF₃ H 8-30 Cl SOMe CHF₂t H 8-31 Cl SOMe C₂F₅ H 8-32 Cl SOMe CH₂OMe H 8-33 Cl SOMe OMe H 8-34 Cl SOMe OEt H 8-35 Cl SOMe OCF₃ H 8-36 Cl SOMe SMe H 8-37 Cl SOMe SOMe H 8-38 Cl SOMe SO₂Me H 8-39 Me SO₂Me H Cl 8-40 Me SO₂Me H Br 8-41 Me SO₂Me H CN 8-42 Me SO₂Me H NO₂ 8-43 Me SO₂Me H Me 8-44 Me SO₂Me H Et 8-45 Me SO₂Me H iPr 8-46 Me SO₂Me H cPr 8-47 Me SO₂Me H tBu 8-48 Me SO₂Me H CF₃ 8-49 Me SO₂Me H CHF₂t 8-50 Me SO₂Me H C₂F₅ 8-51 Me SO₂Me H CH₂OMe 8-52 Me SO₂Me H OMe 8-53 Me SO₂Me H OEt 8-54 Me SO₂Me H OCF₃ 8-55 Me SO₂Me H SMe 8-56 Me SO₂Me H SOMe 8-57 Me SO₂Me H SO₂Me 8-58 Me SO₂Me Cl H 8-59 Me SO₂Me Br H 8-60 Me SO₂Me CN H 8-61 Me SO₂Me NO₂ H 8-62 Me SO₂Me Me H 8-63 Me SO₂Me Et H 8-64 Me SO₂Me iPr H 8-65 Me SO₂Me cPr H 8-66 Me SO₂Me tBu H 8-67 Me SO₂Me CF₃ H 8-68 Me SO₂Me CHF₂t H 8-69 Me SO₂Me C₂F₅ H 8-70 Me SO₂Me CH₂OMe H 8-71 Me SO₂Me OMe H 8-72 Me SO₂Me OEt H 8-73 Me SO₂Me OCF₃ H 8-74 Me SO₂Me SMe H 8-75 Me SO₂Me SOMe H 8-76 Me SO₂Me SO₂Me H

B. FORMULATION EXAMPLES

-   a) A dusting product is obtained by mixing 10 parts by weight of a     compound of the formula (I) and/or salts thereof and 90 parts by     weight of talc as an inert substance and comminuting the mixture in     a hammer mill. -   b) A readily water-dispersible, wettable powder is obtained by     mixing 25 parts by weight of a compound of the formula (I) and/or     salts thereof, 64 parts by weight of kaolin-containing quartz as an     inert substance, 10 parts by weight of potassium lignosulfonate and     1 part by weight of sodium oleoylmethyltaurate as a wetting agent     and dispersant, and grinding the mixture in a pinned-disk mill. -   c) A readily water-dispersible dispersion concentrate is obtained by     mixing 20 parts by weight of a compound of the formula (I) and/or     salts thereof with 6 parts by weight of alkylphenol polyglycol ether     (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether     (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling     range for example about 255 to above 277 C), and grinding the     mixture in a friction ball mill to a fineness of below 5 microns. -   d) An emulsifiable concentrate is obtained from 15 parts by weight     of a compound of the formula (I) and/or salts thereof, 75 parts by     weight of cyclohexanone as a solvent and 10 parts by weight of     ethoxylated nonylphenol as an emulsifier. -   e) Water-dispersible granules are obtained by mixing     -   75 parts by weight of a compound of the formula (I) and/or salts         thereof,     -   10 parts by weight of calcium lignosulfonate,     -   5 parts by weight of sodium lauryl sulfate,     -   3 parts by weight of polyvinyl alcohol and     -   7 parts by weight of kaolin,     -   grinding the mixture in a pinned-disk mill, and granulating the         powder in a fluidized bed by spray application of water as a         granulating liquid. -   f) Water-dispersible granules are also obtained by homogenizing and     precomminuting, in a colloid mill,     -   25 parts by weight of a compound of the formula (I) and/or salts         thereof,     -   5 parts by weight of sodium         2,2′-dinaphthylmethane-6,6′-disulfonate     -   2 parts by weight of sodium oleoylmethyltaurate,     -   1 part by weight of polyvinyl alcohol,     -   17 parts by weight of calcium carbonate and     -   50 parts by weight of water,     -   then grinding the mixture in a bead mill and atomizing and         drying the resulting suspension in a spray tower by means of a         one-phase nozzle.

C. BIOLOGICAL EXAMPLES

1. Pre-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are laid out in sandy loam soil in wood-fiber pots and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then applied to the surface of the covering soil in the form of an aqueous suspension or emulsion at a water application rate equating to 600 to 800 l/ha, with addition of 0.2% wetting agent. After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the trial plants. The damage to the test plants is scored visually after a test period of 3 weeks by comparison with untreated controls (herbicidal activity in percent (%): 100% activity=the plants have died, 0% activity=like control plants).

In this test, for example, compounds no. 2-242 and 2-243 at an application rate of 320 g/ha each show at least 80% efficacy against Echinochloa crus galli, Setaria viridis, Amaranthus retroflexus, Stellaria media, Veronica persica and Viola tricolor.

2. Post-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous and dicotyledonous weed and crop plants are laid out in sandy loam soil in wood-fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then sprayed onto the green parts of the plants in the form of an aqueous suspension or emulsion at a water application rate equating to 600 to 800 l/ha, with addition of 0.2% wetting agent. After the test plants have been left to stand in the greenhouse under optimal growth conditions for about 3 weeks, the action of the preparations is assessed visually in comparison to untreated controls (herbicidal action in percent (%): 100% activity=the plants have died, 0% activity=like control plants).

In this test, for example, compounds no. 2-242 and 2-243 at an application rate of 80 g/ha each show at least 80% efficacy against Echinochloa crus galli, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus, Stellaria media and Viola tricolor. 

The invention claimed is:
 1. An N-(1,3,4-oxadiazol-2-yl)arylcarboxamide of formula (I) or salt thereof

wherein the substituents have the following meanings: A represents N or C—Y, R represents hydrogen or (C₁-C₆)-alkyl, X represents halogen or (C₁-C₆)-alkyl, Y represents halogen, (C₁-C₆)-alkyl, C(O)N(R¹)₂, S(O)_(n)R², or 2-oxoazetidin-1-yl, Z represents halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, or R²(O)_(n)S, V represents hydrogen, halogen or (C₁-C₆)-alkyl, W represents hydrogen, halogen or (C₁-C₆)-haloalkyl, with the proviso that in each case at least one of the radicals V and W does not represent hydrogen, R¹ represents hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R² represents (C₁-C₆)-alkyl, and n represents 0, 1 or 2, with the proviso that the compounds 4-bromo-2,6-difluoro-2-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide and 4-bromo-2,6-difluoro-2-N-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)benzamide are excluded.
 2. The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as claimed in claim 1, wherein R represents hydrogen, or (C₁-C₄)-alkyl, V represents hydrogen, halogen, or (C₁-C₄)-alkyl, and W represents halogen or (C₁-C₄)-haloalkyl.
 3. The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as claimed in claim 1, wherein R represents hydrogen, methyl, or ethyl, X represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, or isopropyl, Y represents fluorine, chlorine, bromine, iodine, (C₁-C₆)-alkyl, or 2-oxoazetidin-1-yl, Z represents fluorine, chlorine, bromine iodine, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, or heptafluoroisopropyl, V represents hydrogen, fluorine, or methyl and, W represents fluorine.
 4. The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as claimed in claim 1, wherein A represents C—Y, V represents hydrogen, and W represents fluorine.
 5. The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as claimed in claim 1, wherein A represents C—Y, R represents hydrogen, methyl, or ethyl, X represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, or isopropyl, V represents hydrogen, and W represents fluorine.
 6. The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as claimed in claim 5, wherein Y represents S(O)_(n)R², and Z represents trifluoromethyl, difluoromethyl or pentafluoroethyl.
 7. The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as claimed in claim 5, wherein X represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, or isopropyl, Y represents fluorine, chlorine, methyl ethyl, propyl, isopropyl, CONMe₂, S(O)Me, S(O)Et, So₂Me, or SO₂Et, and Z represents fluorine, chlorine, bromine, iodine, CF₃, SMe, SEt, SOMe, SOEt, SO₂Me, or SO₂Et.
 8. The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as claimed in claim 1, wherein A represents N, V represents hydrogen, W represents fluorine, and Z represents CF₃.
 9. An herbicidal composition, comprising an herbicidally active content of at least one compound of formula (I) as claimed in claim
 1. 10. The herbicidal composition as claimed in claim 9 in a mixture with one or more formulation auxiliaries.
 11. The herbicidal composition as claimed in claim 9, comprising at least one further pesticidally active substance from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners, and growth regulators.
 12. The herbicidal composition as claimed in claim 11, comprising a safener.
 13. The herbicidal composition as claimed in claim 12, comprising cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.
 14. The herbicidal composition as claimed in claim 9, comprising a further herbicide.
 15. A method for controlling monocotyledonous or dicotyledonous weeds, comprising applying an effective amount of at least one compound of formula (I) as claimed in claim 1 or of a herbicidal composition comprising the at least one compound of formula (I) is applied to the weeds or to the site of the weeds.
 16. A product comprising the compound of formula (I) as claimed in claim 1 or an herbicidal composition comprising the compound of formula (I) for controlling one or more monocotyledonous or dicotyledonous weeds. 